Aminoacetonitrile derivatives and their use for controlling parasites

ABSTRACT

The invention relates to compounds of the general formula  
                 
 
in which R 1 , R 2 , X, Ar 1  and Ar 2  are as defined in claim  1 , and to any enantiomers thereof. The active ingredients have advantageous pesticidal properties. They are particularly suitable for controlling parasites in warm-blooded animals.

The present invention relates to novel amidoacetonitrile compounds ofthe formula

in whichAr₁ and Ar₂ are, independently of one another, unsubstituted or mono- orpolysubstituted phenyl, in which the substituents can be independent ofone another and are chosen from the group consisting of halogen, nitro,cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₂-C₆alkenyl, halo-C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl,C₃-C₆cycloalkyloxy, C₃-C₆cycloalkylamino, C₃-C₆cycloalkylthio,C₂-C₆alkenyloxy, halo-C₂-C₆alkenyloxy, C₁-C₆alkylthio,halo-C₁-C₆alkylthio, C₁-C₆alkylsulfonyloxy, halo-C₁-C₆alkylsulfonyloxy,C₁-C₆alkylsulfinyl, halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,halo-C₁-C₆alkylsulfonyl, C₂-C₆alkenylthio, halo-C₂-C₆alkenylthio,C₂-C₆alkenylsulfinyl, halo-C₂-C₆alkenylsulfinyl, C₂-C₆alkenylsulfonyl,halo-C₂-C₆alkenylsulfonyl, C₁-C₆alkylamino, di-C₁-C₆alkylamino,C₁-C₆alkylsulfonylamino, halo-C₁-C₆alkylsulfonylamino,C₁-C₆alkylcarbonyl, halo-C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆alkylaminocarbonyl and di-C₁-C₆alkylaminocarbonyl; unsubstituted ormono- or polysubstituted phenylamino; unsubstituted or mono- orpolysubstituted phenylcarbonyl; unsubstituted or mono- orpolysubstituted phenylmethoxyimino; unsubstituted or mono- orpolysubstituted phenylhydroxymethyl; unsubstituted or mono- orpolysubstituted 1-phenyl-1-hydroxyethyl; unsubstituted or mono- orpolysubstituted phenylchloromethyl; unsubstituted or mono- orpolysubstituted phenylcyanomethyl; unsubstituted or mono- orpolysubstituted phenyl, in which the substituents in each case can beindependent of one another and are chosen from the group consisting ofhalogen, nitro, cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,halo-C₁-C₆alkoxy, C₁-C₆alkylthio, halo-C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl andhalo-C₁-C₆alkylsulfonyl; unsubstituted or mono- or polysubstitutedphenoxy, in which the substituents can be independent of one another andare chosen from the group consisting of halogen, nitro, cyano,C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl and halo-C₁-C₆alkylsulfonyl;unsubstituted or mono- or polysubstituted phenylacetylenyl, in which thesubstituents can be independent of one another and are chosen from thegroup consisting of halogen, nitro, cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl,C₁-C₆alkoxy, halo-C₁-C₆alkoxy, C₁-C₆alkylthio, halo-C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl andhalo-C₁-C₆alkylsulfonyl; and unsubstituted or mono- or polysubstitutedpyridyloxy, in which the substituents can be independent of one anotherand are chosen from the group consisting of halogen, nitro, cyano,C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl and halo-C₁-C₆alkylsulfonyl;unsubstituted or mono- or polysubstituted hetaryl, in which thesubstituents can be independent of one another and are chosen from thegroup consisting of halogen, nitro, cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl,C₁-C₆alkoxy, halo-C₁-C₆alkoxy, C₂-C₆alkenyloxy, halo-C₂-C₆alkenyloxy,C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,halo-C₁-C₆alkylsulfinyl, C₂-C₆alkenylthio, halo-C₂-C₆alkenylthio,C₂-C₆alkenylsulfinyl, halo-C₂-C₆alkenylsulfinyl, C₁-C₆alkylsulfonyl,halo-C₁-C₆alkylsulfonyl, C₂-C₆alkenylsulfonyl,halo-C₂-C₆alkenylsulfonyl, C₁-C₆alkylamino and di-C₁-C₆alkylamino; orunsubstituted or mono- or polysubstituted naphthyl or quinolyl, in whichthe substituents can be independent of one another and are chosen fromthe group consisting of halogen, nitro, cyano, C₁-C₆alkyl,halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy, C₂-C₆alkenyloxy,halo-C₂-C₆alkenyloxy, C₁-C₆alkylthio, halo-C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, halo-C₁-C₆alkylsulfinyl, C₂-C₆alkenylthio,halo-C₂-C₆alkenylthio, C₂-C₆alkenylsulfinyl, halo-C₂-C₆alkenylsulfinyl,C₁-C₆alkylsulfonyl, halo-C₁-C₆alkylsulfonyl, C₂-C₆alkenylsulfonyl,halo-C₂-C₆alkenylsulfonyl, C₁-C₆alkylamino and di-C₁-C₆alkylamino;R₁ is hydrogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, allyl or C₁-C₆alkoxymethyl;R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are either, independently of one another,hydrogen, halogen, unsubstituted or mono- or polyhalogenated C₁-C₆alkyl,unsubstituted or mono- or polyhalogenated C₂-C₆alkenyl, unsubstituted ormono- or polyhalogenated C₂-C₆alkynyl; unsubstituted or mono- orpolysubstituted C₁-C₆alkoxy, unsubstituted or mono- or polysubstitutedhalo-C₁-C₆alkoxy, unsubstituted or mono- or polysubstitutedC₃-C₆cycloalkyl, in which the substituents in each case can beindependent of one another and are chosen from the group consisting ofhalogen and C₁-C₆alkyl; or unsubstituted or mono- or polysubstitutedphenyl, in which the substituents can be independent of one another andare chosen from the group consisting of halogen, nitro, cyano,C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, halo-C₁-C₆alkylsulfonyl,C₁-C₆alkylamino or di-C₁-C₆alkylamino;or R₂ and R₃ are jointly C₂-C₆alkylene; andX is C(R₃)(R₄)—C(R₅)(R₆) or C(R₇)═C(R₈);to their preparation and use in the control of endo- and ectoparasites,especially helminths, in and on warm-blooded productive livestock,domestic animals and plants, and also to pesticides which comprise atleast one of these compounds.

Substituted amidoacetonitrile compounds with pesticidal action aredisclosed in EP-O 953 565 A2, for example. The active ingredientsspecifically revealed therein may not, however, always meet therequirements concerning strength and activity spectrum. Thereconsequently exists a need for active ingredients with improvedpesticidal properties. It has now been found that the amidoacetonitrilecompounds of the formula I have outstanding pesticidal properties, inparticular against endo- and ectoparasites in and on productivelivestock, domestic animals and plants.

Alkyl—as group per se and as structural component of other groups andcompounds, for example of haloalkyl, alkoxy, alkylthio, alkylsulfinyland alkylsulfonyl,—is, in each case giving due consideration to thenumber of carbon atoms which the relevant group or compound has in eachindividual case, either straight-chain, i.e. methyl, ethyl, propyl,butyl, pentyl or hexyl, or branched, e.g. isopropyl, isobutyl,sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.

Alkenyl—as group per se and as structural component of other groups andcompounds—is, in each case giving due consideration to the number ofcarbon atoms and conjugated or isolated double bonds which the relevantgroup or compound has in each individual case, either straight-chain,e.g. allyl, 2-butenyl, 3-pentenyl, 1-hexenyl or 1,3-hexadienyl, orbranched, e.g. isopropenyl, isobutenyl, isoprenyl, tert-pentenyl orisohexenyl.

Alkynyl—as group per se and as structural component of other groups andcompounds—is, in each case giving due consideration to the number ofcarbon atoms and conjugated or isolated double bonds which the relevantgroup or compound has in each individual case, either straight-chain,e.g. propargyl, 2-butynyl, 3-pentynyl, 1-hexynyl, 1-heptynyl or3-hexen-1-ynyl, or branched, e.g. 3-methylbut-1-ynyl, 4-ethylpent-1-ynylor 4-methylhex-2-ynyl.

Cycloalkyl—as group per se and as structural component of other groupsand compounds, for example of halocycloalkyl, cycloalkoxy orcycloalkylthio,—is, in each case giving due consideration to the numberof carbon atoms which the relevant group or compound has in eachindividual case, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Hetaryl is pyridyl, pyrimidyl, s-triazinyl, 1,2,4-triazinyl, thienyl,furanyl, pyrroyl, pyrazolyl, imidazolyl, thiazolyl, triazolyl, oxazolyl,thiadiazolyl, oxadiazolyl, benzothienyl, benzofuranyl, benzothiazolyl,indolyl or indazolyl, preferably pyridyl, pyrimidyl, s-triazinyl or1,2,4-triazinyl, in particular pyridyl or pyrimidyl.

Halogen—as group per se and as structural component of other groups andcompounds, such as of haloalkyl, haloalkoxy, haloalkylthio,haloalkylsulfinyl and haloalkylsulfonyl,—is fluorine, chlorine, bromineor iodine, in particular fluorine, chlorine or bromine, especiallyfluorine or chlorine.

Halogen-substituted carbon-comprising groups and compounds, such ashaloalkyl, halo-alkoxy, haloalkylthio, haloalkylsulfinyl andhaloalkylsulfonyl, can be partially halogenated or perhalogenated, itbeing possible, in the case of polyhalogenation, for the halogensubstituents to be identical or different. Examples of haloalkyl—asgroup per se and as structural component of other groups and compounds,such as of haloalkoxy or haloalkylthio,—are methyl substituted up tothree times by fluorine, chlorine and/or bromine, such as CHF₂ or CF₃;ethyl substituted up to five times by fluorine, chlorine and/or bromine,such as CH₂CF₃, CF₂CF₃, CF₂CCl₃, CF₂CHCl₂, CF₂CHF₂, CF₂CFCl₂, CF₂CHBr₂,CF₂CHClF, CF₂CHBrF or CClFCHClF; propyl or isopropyl substituted up toseven times by fluorine, chlorine and/or bromine, such as CH₂CHBrCH₂Br,CF₂CHFCF₃, CH₂CF₂CF₃ or CH(CF₃)₂; butyl or one of its isomerssubstituted up to nine times by fluorine, chlorine and/or bromine, suchas CF(CF₃)CHFCF₃ or CH₂(CF₂)₂CF₃; pentyl or one of its isomerssubstituted up to eleven times by fluorine, chlorine and/or bromine,such as CF(CF₃)(CHF)₂CF₃ or CH₂(CF₂)₃CF₃; and hexyl or one of itsisomers substituted up to thirteen times by fluorine, chlorine and/orbromine, such as (CH₂)₄CHBrCH₂Br, CF₂(CHF)₄CF₃, CH₂(CF₂)₄CF₃ orC(CF₃)₂(CHF)₂CF₃.

Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Forexample, alkoxy is methoxy, ethoxy, propoxy, isopropoxy, n-butoxy,isobutoxy, sec-butoxy and tert-butoxy, and also the pentyloxy andhexyloxy isomers; preferably methoxy and ethoxy. Haloalkoxy groupspreferably have a chain length of 1 to 6 carbon atoms. Haloalkoxy is,e.g., fluoromethoxy, difluoromethoxy, trifluoromethoxy,2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy,2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferablydifluoromethoxy, 2-chlooroethoxy and trifluoromethoxy.

Preferred embodiments within the context of the invention are:

(1) a compound of the formula I, in which Ar₁ and Ar₂ are, independentlyof one another, unsubstituted or mono- or polysubstituted phenyl, inwhich the substituents can be independent of one another and are chosenfrom the group consisting of halogen, nitro, cyano, C₁-C₄alkyl,halo-C₁-C₄alkyl, C₁-C₄alkoxy, halo-C₁-C₄alkoxy, C₃-C₅Cycloalkyl,C₃-C₅cycloalkyloxy, C₃-C₅cycloalkylamino, C₁-C₅alkylthio,halo-C₁-C₅alkylthio, C₁-C₄alkylamino, di-C₁-C₄alkylamino,C₁-C₄alkylcarbonyl, halo-C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylaminocarbonyl and di-C₁-C₄alkylaminocarbonyl; unsubstituted ormono- or polysubstituted phenylamino; unsubstituted or mono- orpolysubstituted phenylcarbonyl; unsubstituted or mono- orpolysubstituted phenyl, in which the substituents in each case can beindependent of one another and are chosen from the group consisting ofhalogen, nitro, cyano, C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy,halo-C₁-C₄alkoxy, C₁-C₄alkylthio and halo-C₁-C₄alkylthio; unsubstitutedor mono- or polysubstituted phenoxy, in which the substituents can beindependent of one another and are chosen from the group consisting ofhalogen, nitro, cyano, C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy,halo-C₁-C₄alkoxy, C₁-C₄alkylthio and halo-C₁-C₄alkylthio; andunsubstituted or mono- or polysubstituted pyridyloxy, in which thesubstituents can be independent of one another and are chosen from thegroup consisting of halogen, nitro, cyano, C₁-C₄alkyl, halo-C₁-C₄alkyl,C₁-C₄alkoxy, halo-C₁-C₄alkoxy, C₁-C₄alkylthio and halo-C₁-C₄alkylthio;

particularly, independently of one another, unsubstituted or mono- orpolysubstituted phenyl, in which the substituents can be independent ofone another and are chosen from the group consisting of halogen, nitro,cyano, C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy, halo-C₁-C₄alkoxy,C₃-C₅cycloalkyl, C₃-C₅cycloalkyloxy, C₃-C₅cycloalkylamino,C₁-C₄alkylcarbonyl, halo-C₁-C₄alkylcarbonyl and C₁-C₄alkoxycarbonyl;unsubstituted or mono- or polysubstituted phenylamino; unsubstituted ormono- or polysubstituted phenylcarbonyl; unsubstituted or mono- orpolysubstituted phenyl, in which the substituents in each case can beindependent of one another and are chosen from the group consisting ofhalogen, nitro, cyano, C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy andhalo-C₁-C₄alkoxy; and unsubstituted or mono- or polysubstituted phenoxy,in which the substituents can be independent of one another and arechosen from the group consisting of halogen, nitro, cyano, C₁-C₄alkyl,halo-C₁-C₄alkyl, C₁-C₄alkoxy and halo-C₁-C₄alkoxy;

very particularly, independently of one-another, unsubstituted or mono-or polysubstituted phenyl, in which the substituents can be independentof one another and are chosen from the group consisting of halogen,cyano, C₁-C₂alkyl, halo-C₁-C₂alkyl, C₁-C₂alkoxy, halo-C₁-C₂alkoxy,C₃-C₄cycloalkyl, C₃-C₄cycloalkyloxy, C₃-C₄cycloalkylamino,C₁-C₂alkylcarbonyl, halo-C₁-C₂alkylcarbonyl and C₁-C₂alkoxycarbonyl;unsubstituted or mono- or polysubstituted phenylamino; unsubstituted ormono- or polysubstituted phenylcarbonyl; unsubstituted or mono- orpolysubstituted phenyl, in which the substituents in each case can beindependent of one another and are chosen from the group consisting ofhalogen, cyano, C₁-C₂alkyl, halo-C₁-C₂alkyl, C₁-C₂alkoxy andhalo-C₁-C₂alkoxy; and unsubstituted or mono- or polysubstituted phenoxy,in which the substituents can be independent of one another and arechosen from the group consisting of halogen, cyano, C₁-C₂alkyl,halo-C₁-C₂alkyl, C₁-C₂alkoxy and halo-C₁-C₂alkoxy;

(2) a compound of the formula I, in which R₁ is hydrogen, C₁-C₄alkyl orhalo-C₁-C₄alkyl; particularly hydrogen or C₁-C₂alkyl;

very particularly hydrogen;

(3) a compound of the formula I, in which R₂, R₃, R₄, R₅, R₆, R₇ and R₈are, independently of one another, hydrogen, halogen, unsubstituted ormono- or polyhalogenated C₁-C₄alkyl, unsubstituted or mono- orpolyhalogenated C₂-C₄alkenyl, unsubstituted or mono- or polyhalogenatedC₂-C₄alkynyl; unsubstituted or mono- or polysubstituted C₁-C₄alkoxy,unsubstituted or mono- or polysubstituted halo-C₁-C₄alkoxy,C₃-C₅cycloalkyl, or unsubstituted or mono- or polysubstituted phenyl, inwhich the substituents can be independent of one another and are chosenfrom the group consisting of halogen, cyano, C₁-C₄alkyl,halo-C₁-C₄alkyl, C₁-C₄alkoxy and halo-C₁-C₄alkoxy;

particularly, independently of one another, hydrogen, unsubstituted ormono- or polyhalogenated C₁-C₄alkyl, C₃-C₅cycloalkyl, or unsubstitutedor mono- or polysubstituted phenyl, in which the substituents can beindependent of one another and are chosen from the group consisting ofhalogen, C₁-C₂alkyl or halo-C₁-C₄alkyl;

very particularly, independently of one another, hydrogen, C₁-C₂alkyl orC₃-C₅cycloalkyl;

(4) a compound of the formula I, in which X is C(R₃)(R₄)—C(R₅)(R₆);

(5) a compound of the formula I, in which Ar₁ and Ar₂ are, independentlyof one another, unsubstituted or mono- or polysubstituted phenyl, inwhich the substituents can be independent of one another and are chosenfrom the group consisting of halogen, nitro, cyano, C₁-C₄alkyl,halo-C₁-C₄-alkyl, C₁-C₄alkoxy, halo-C₁-C₄alkoxy, C₃-C₅cycloalkyl,C₃-C₅cycloalkyloxy, C₃-C₅cycloalkylamino, C₁-C₅alkylthio,halo-C₁-C₅alkylthio, C₁-C₄alkylamino, di-C₁-C₄alkylamino,C₁-C₄alkylcarbonyl, halo-C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylaminocarbonyl and di-C₁-C₄alkylaminocarbonyl; unsubstituted ormono- or polysubstituted phenylamino; unsubstituted or mono- orpolysubstituted phenylcarbonyl; unsubstituted or mono- orpolysubstituted phenyl, in which the substituents in each case can beindependent of one another and are chosen from the group consisting ofhalogen, nitro, cyano, C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy,halo-C₁-C₄alkoxy, C₁-C₄alkylthio and halo-C₁-C₄alkylthio; unsubstitutedor mono- or polysubstituted phenoxy, in which the substituents can beindependent of one another and are chosen from the group consisting ofhalogen, nitro, cyano, C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy,halo-C₁-C₄alkoxy, C₁-C₄alkylthio and halo-C₁-C₄alkylthio; andunsubstituted or mono- or polysubstituted pyridyloxy, in which thesubstituents can be independent of one another and are chosen from thegroup consisting of halogen, nitro, cyano, C₁-C₄alkyl, halo-C₁-C₄alkyl,C₁-C₄alkoxy, halo-C₁-C₄alkoxy, C₁-C₄alkylthio and halo-C₁-C₄alkylthio;

R₁ is hydrogen, C₁-C₄alkyl or halo-C₁-C₄alkyl;

R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are, independently of one another,hydrogen, halogen, unsubstituted or mono- or polyhalogenated C₁-C₄alkyl,unsubstituted or mono- or polyhalogenated C₂-C₄alkenyl, unsubstituted ormono- or polyhalogenated C₂-C₄alkynyl; unsubstituted or mono- orpolysubstituted C₁-C₄alkoxy, unsubstituted or mono- or polysubstitutedhalo-C₁-C₄alkoxy, C₃-C₅cycloalkyl, or unsubstituted or mono- orpolysubstituted phenyl, in which the substituents can be independent ofone another and are chosen from the group consisting of halogen, cyano,C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy and halo-C₁-C₄alkoxy; and

X is C(R₃)(R₄)—C(R₅)(R₆);

(6) a compound of the formula I, in which Ar₁ and Ar₂ are particularly,independently of one another, unsubstituted or mono- or polysubstitutedphenyl, in which the substituents can be independent of one another andare chosen from the group consisting of halogen, nitro, cyano,C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy, halo-C₁-C₄alkoxy,C₃-C₅cycloalkyl, C₃-C₅cycloalkyloxy, C₃-C₅cycloalkylamino,C₁-C₄alkylcarbonyl, halo-C₁-C₄alkylcarbonyl and C₁-C₄alkoxycarbonyl;unsubstituted or mono- or polysubstituted phenylamino; unsubstituted ormono- or polysubstituted phenylcarbonyl; unsubstituted or mono- orpolysubstituted phenyl, in which the substituents in each case can beindependent of one another and are chosen from the group consisting ofhalogen, nitro, cyano, C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy andhalo-C₁-C₄alkoxy; and unsubstituted or mono- or polysubstituted phenoxy,in which the substituents can be independent of one another and arechosen from the group consisting of halogen, nitro, cyano, C₁-C₄alkyl,halo-C₁-C₄alkyl, C₁-C₄alkoxy and halo-C₁-C₄alkoxy;

R₁ is hydrogen or C₁-C₂alkyl;

R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are, independently of one another,hydrogen, unsubstituted or mono- or polyhalogenated C₁-C₄alkyl,C₃-C₅cycloalkyl, or unsubstituted or mono- or polysubstituted phenyl, inwhich the substituents can be independent of one another and are chosenfrom the group consisting of halogen, C₁-C₂alkyl or halo-C₁-C₄alkyl; and

X is C(R₃)(R₄)—C(R₅)(R₆);

(7) a compound of the formula I, in which Ar₁ and Ar₂ are, independentlyof one another, unsubstituted or mono- or polysubstituted phenyl, inwhich the substituents can be independent of one another and are chosenfrom the group consisting of halogen, cyano, C₁-C₂alkyl,halo-C₁-C₂alkyl, C₁-C₂alkoxy, halo-C₁-C₂alkoxy, C₃-C₄cycloalkyl,C₃-C₄cyclo-alkyloxy, C₃-C₄cycloalkylamino, C₁-C₂alkylcarbonyl,halo-C₁-C₂alkylcarbonyl and C₁-C₂alkoxycarbonyl; unsubstituted or mono-or polysubstituted phenylamino; unsubstituted or mono- orpolysubstituted phenylcarbonyl; unsubstituted or mono- orpolysubstituted phenyl, in which the substituents in each case can beindependent of one another and are chosen from the group consisting ofhalogen, cyano, C₁-C₂alkyl, halo-C₁-C₂alkyl, C₁-C₂alkoxy andhalo-C₁-C₂alkoxy; and unsubstituted or mono- or polysubstituted phenoxy,in which the substituents can be independent of one another and arechosen from the group consisting of halogen, cyano, C₁-C₂alkyl,halo-C₁-C₂alkyl, C₁-C₂alkoxy and halo-C₁-C₂alkoxy;

R₁ is hydrogen;

R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are, independently of one another,hydrogen, C₁-C₂alkyl or C₃-C₅cycloalkyl; and

X is C(R₃)(R₄)—C(R₅)(R₆).

The compounds of the formula I listed in Table 1 are particularlypreferred within the context of the invention and the compounds of theformula I mentioned in the synthetic examples are very particularlypreferred.

A further subject-matter of the invention is the process for thepreparation of the compounds of the formula I, in each case in the freeform or in the salt form, e.g. which comprises the reaction of acompound of the formula

which is known or can be prepared by analogy to relevant known compoundsand in which R₁, R₂, X and Ar₂ are as defined above in the formula I,with a compound of the formula

which is known or can be prepared by analogy to relevant known compoundsand in which Ar₁ is as defined above in the formula I and Q is a leavinggroup, if desired in the presence of a basic catalyst, and in each case,if desired, the conversion of a compound of the formula I obtainableaccording to the process or in another way, in each case in the freeform or in the salt form, to another compound of the formula I, theseparation of a mixture of isomers obtainable according to the processand the isolation of the desired isomer and/or the conversion of a freecompound of the formula I obtainable according to the process to thesalt or the conversion of a salt of a compound of the formula Iobtainable according to the process to the free compound of the formulaI or to another salt.

That which has been said above for salts of compounds I appliesanalogously to starting materials mentioned hereinabove and hereinafterwith regard to the salts thereof.

The reactants can be reacted with one another as such, i.e. withoutaddition of a solvent or diluent, e.g. in the molten form. For the mostpart, however, it is advantageous to add an inert solvent or diluent ora mixture thereof. Mention may be made, as examples of such solvents ordiluents, of: aromatic, aliphatic and alicyclic hydrocarbons andhalogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene,tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether,hexane, cyclohexane, dichloromethane, trichloromethane,tetrachloromethane, dichloroethane, trichloroethene ortetrachloroethene; ethers, such as diethyl ether, dipropyl ether,diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethyleneglycol monomethyl ether, ethylene glycol monoethyl ether, ethyleneglycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran ordioxane; ketones, such as acetone, methyl ethyl ketone or methylisobutyl ketone; amides, such as N,N-dimethylformamide,N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone orhexamethylphosphoramide; nitriles, such as acetonitrile orpropionitrile; and sulfoxides, such as dimethyl sulfoxide.

Preferred leaving groups Q are halogens, tosylates, mesylates andtriflates, particularly preferably halogens, especially chlorine.

Suitable bases for facilitating the reaction are, e.g., alkali metal oralkaline earth metal hydroxides, hydrides, amides, alkoxides, acetates,carbonates, dialkylamides or alkyl-silylamides, alkylamines,alkylenediamines, if desired N-alkylated and saturated or unsaturated,cycloalkylamines, basic heterocycles, ammonium hydroxides andcarbocyclic amines. Mention may be made, by way of examples, of sodiumhydroxide, sodium hydride, sodamide, sodium methoxide, sodium acetate,sodium carbonate, potassium t-butoxide, potassium hydroxide, potassiumcarbonate, potassium hydride, lithium diisopropylamide, potassiumbis(trimethylsilyl)amide, calcium hydride, triethylamine,diisopropylethylamine, triethylenediamine, cyclohexylamine,N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine,4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine,benzyltrimethylammonium hydroxide and 1,5-diazabicyclo[5.4.0]undec-5-ene(DBU). Diisopropylethylamine and 4-(N,N-dimethylamino)pyridine arepreferred.

The reaction is advantageously carried out at a temperature fromapproximately 0° C. to approximately +100° C., preferably fromapproximately 10° C. to approximately +40° C.

In a preferred process, a compound of the formula II is reacted atambient temperature in a halogenated hydrocarbon, preferablydichloromethane, with a compound of the formula III in the presence of abase, preferably a mixture of diisopropylethylamine and4-(N,N-dimethylamino)pyridine.

A further subject-matter of the invention is the process for thepreparation of the compounds of the formula II, in each case in the freeform or in the salt form, e.g. which comprises the reaction of acompound of the formula

which is known or can be prepared by analogy to relevant known compoundsand in which R₂, X and Ar₂ are as defined in formula I, with aninorganic or organic cyanide and a compound of the formula R₁—NH₂, whichIs known or can be prepared by analogy to relevant known compounds andin which R₁ is as defined in the formula I, and in each case, ifdesired, the conversion of a compound of the formula II obtainableaccording to the process or in another way, In each case in the freeform or in the salt form, to another compound of the formula II, theseparation of a mixture of isomers obtainable according to the processand the isolation of the desired isomer and/or the conversion of a freecompound of the formula II obtainable according to the process to a saltor the conversion of a salt of a compound of the formula II obtainableaccording to the process to the free compound of the formula II or toanother salt.

Suitable cyanides are sodium cyanide, potassium cyanide, trimethylsilylcyanide and acetone cyanohydrin.

The general method for the reaction of carbonyl compounds, for exampleof the formula IV, with cyanides and amines, for example of the formulaR₆—NH₂, is known as a Strecker reaction, for example in OrganicSynthesis Coll. Vol. 3, 88 (1973).

Salts of compounds I can be prepared in a way known per se. Thus, forexample, acid addition salts of compound I are obtained by treatmentwith a suitable acid or a suitable ion-exchange reagent and salts withbases are obtained by treatment with a suitable base or a suitableion-exchange reagent.

Salts of compounds I can be converted in the usual way to the freecompounds I, acid addition salts, e.g. by treatment with a suitablebasic agent or a suitable ion exchange reagent, and salts with bases,e.g. by treatment with a suitable acid or a suitable ion-exchangereagent.

Salts of compounds I can be changed in a way known per se to other saltsof compounds I, acid addition salts for example to other acid additionsalts, e.g. by treatment of a salt of an inorganic acid, such as ahydrochloride, with a suitable metal salt, such as a sodium, barium orsilver salt, of an acid, e.g. with silver acetate, in a suitablesolvent, in which an inorganic salt, e.g. silver chloride, being formedis insoluble and for this reason precipitates from the reaction mixture.

According to the method or reaction conditions, the compounds I withsalt-forming properties can be obtained in the free form or in the formof salts.

The compounds I can also be obtained in the form of their hydratesand/or can incorporate other solvents, which might, for example, be usedin the crystallization of compounds existing in the solid form.

The compounds I can exist as optical and/or geometrical isomers ormixtures thereof. The invention relates both to the pure isomers and toall possible mixtures of isomers and is to, be correspondinglyunderstood in each case heretofore and hereinafter, even ifstereochemical details are not specifically referred to in every case.

Mixtures of diastereoisomers and mixtures of racemates of compounds Iobtainable according to the process—depending on the choice of thestarting materials and operating methods—or otherwise obtainable can beseparated in a known way into the pure diastereoisomers or racemates onthe basis of the physicochemical differences of the components, forexample by fractional crystallization, distillation and/orchromatography.

Correspondingly obtainable mixtures of enantiomers, such as racemates,can be resolved into the optical isomers by known methods, for exampleby recrystallization from an optically active solvent, by chromatographyon chiral adsorbents, e.g. high performance liquid chromatography (HPLC)on acetylcellulose, with the help of suitable microorganisms, bycleavage with specific immobilized enzymes, via the formation ofinclusion complexes, e.g. by using chiral crown ethers, in which onlyone enantiomer is complexed.

In addition to through separation of the corresponding mixtures ofisomers, pure diastereoisomers or enantiomers according to the inventioncan also be obtained through generally known methods ofdiastereoselective or enantioselective synthesis, e.g. by carrying outthe process according to the invention with educts with correspondinglysuitable stereochemistry.

Advantageously, the biologically most effective isomer, e.g. enantiomer,or mixture of isomers, e.g. mixture of enantiomers, is isolated orsynthesized each time, provided that the individual components havedifferent biological activity.

In the process of the present invention, use is preferably made of suchstarting materials and intermediates which result in the compounds Idescribed at the beginning as particularly valuable.

The invention relates in particular to the preparation process describedin the examples.

Starting materials and intermediates used according to the invention forthe preparation of the compounds I which are novel, their use andprocesses for their preparation likewise form a subject-matter of theinvention.

The compounds I according to the invention are characterized by aparticularly broad activity spectrum and are valuable active ingredientsin the field of pest control which are well tolerated by warm-bloodedspecies, fish and plants, including in particular for controlling endo-and ecto parasites which parasitize animals.

In the context of the present invention, the term “ectoparasites” isunderstood to mean, in particular, insects, mites and ticks. Thisincludes insects of the orders: Lepidoptera, Coleoptera, Homoptera,Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera,Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera. However,reference may in particular be made to ectoparasites which are anuisance to man or animals and which transmit pathogens, for exampleflies, such as Musca domestica, Musca vetustissima, Musca autumnalis,Fannia canicularis, Sarcophaga carnaria, Lucilia cuprina, Hypodermabovis, Hypoderma lineatum, Chiysomyia chloropyga, Dermatobia hominis,Cochliomyia hominivorax, Gasterophilus intestinalis, Oestrus ovis,Stomoxys calcitrans, Haematobia irritans, and mosquitoes (Nematocera),such as Culicidae, Simuliidae, Psychodidae, but also bloodsuckingparasites, for example fleas, such as Ctenocephalides felis andCtenocephalides canis (cat and dog fleas), Xenopsylla cheopis, Pulexirritans, Dermatophilus penetrans, lice, such as Damalina ovis,Pediculus humanis, stable flies and horse flies (Tabanidae), Haematopotaspp., such as Haematopota pluvialis, Tabanidea spp., such as Tabanusnigrovittatus, Chtysopsinae spp., such as Chlysops caecutiens, tsetseflies, such as Glossinia species, biting insects, in particularcockroaches, such as Blatella germanica, Blatta orientalis, Periplanetaamericana, mites, such as Dermanyssus gamlinae, Sarcoptes scabiel,Psoroptes ovis and Psorergates spp., and last but not least ticks. Thelatter belong to the order Acarina. Known representatives of ticks are,e.g., Boophilus, Amblyomma, Anocentor, Dermacentor, Haemaphysalis,Hyalomma, Ixodes, Rhipicentor, Margaropus, Rhipicephalus, Argas, Otobiusand Omithodoros and the like, which preferably infest warm-bloodedanimals, including farm animals, such as cows, pigs, sheep and goats,poultry, such as chickens, turkeys and geese, fur-bearing animals, suchas mink, foxes, chinchillas, rabbits and the like, and pets, such ascats and dogs, but also man.

The compounds I according to the invention are also effective againstall or individual development stages of normally sensitive but also ofresistant animal pests, such as insects and representatives of the orderAcarina. The insecticidal, ovicidal and/or acaricidal action of theactive ingredients according to the invention may in the process bedisplayed directly, i.e. in killing the pests, immediately or only aftersome time, for example during moulting, or their eggs, or indirectly,e.g. in reduced egg laying and/or in a reduced hatching rate, in whichthe good action corresponds to a kill rate (mortality) of at least 50 to60%.

The compounds I can also be used against hygiene pests, in particular ofthe order Diptera with the families Sarcophagidae, Anophilidae andCulicidae; of the orders Orthoptera, Dictyoptera (e.g. the familyBlattidae) and Hymenoptera (e.g. the family Formicidae).

The compounds I also have lasting activity in the case of phytoparasiticmites and insects. In the case of spider mites of the order Acarina,they are active against eggs, nymphs and adults of Tetranychidae(Tetranychus spp. and Panonychus spp.).

They are highly active in the case of the sucking insects of the orderHomoptera, in particular against pests of the families Aphididae,Delphacidae, Cicadellidae, Psyllidae, Loccidae, Diaspididae andEriophydidae (e.g. citrus rust mite); of the orders Hemiptera,Heteroptera and Thysanoptera, and in the case of the phytophagousinsects of the orders Lepidoptera, Coleoptera, Diptera and Orthoptera.

They are also suitable as soil insecticides against pests in the soil.

The compounds of the formula I are accordingly active against alldevelopment stages of sucking and feeding insects on crops such ascereals, cotton, rice, maize, soya beans, potatoes, vegetables, fruit,tobacco, hops, citrus fruit, avocados and others.

The compounds of the formula I are also active against plant nematodesof the genera Meloidogyne, Heterodera, Pratylenchus, Ditylenchus,Radopholus, Rizoglyphus and others.

The compounds are particularly active against helminths, among which theendoparasitic nematodes and trematodes can be the cause of seriousdiseases in mammals and poultry, e.g. in sheep, pigs, goats, cattle,horses, donkeys, dogs, cats, guinea pigs and ornamental birds. Typicalnematodes of this indication are: Haemonchus, Trichostrongylus,Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostonum, Oesophagostonum,Chabertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria,Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria,Toxascaris and Parascaris. Mention may specifically be made, among thetrematodes, of the family of the Fasciolideae, in particular Fasciolahepatica. The particular advantage of the compounds of the formula I istheir activity against such parasites, which are resistant tobenzimidazole-based active ingredients.

Certain species of the genera Nematodirus, Cooperia and Oesophagostonumattack the intestinal tract of the host animal, while others of thegenera Haemonchus and Ostertagia parasitize in the stomach and others ofthe genus Dictyocaulus parasitize in lung tissue. Parasites of thefamilies Filariidae and Setariidae are found in internal cell tissue andin organs, e.g. the heart, blood vessels, lymph vessels and subcutaneoustissue. Mention may particularly be made here of the dog heartworm,Dirofilaria immitis. The compounds of the formula I are highly effectiveagainst these parasites.

The pests which can be controlled with the compounds of the formula Ialso include, from the class Cestoda (tapeworms), the familiesMesocestoidae, In particular the genus Mesocestoides, especially M.lineatus; Dilepididae, in particular Dipylidium caninum, Joyeuxiellaspp., especially Joyeuxiella pasquali, and Diplopylidium spp.; andTaeniidae, in particular Taenia pisiformis, Taenia cervi, Taenia ovis,Taneia hydatigena, Taenia multiceps, Taenia taeniaeformis, Taeniaserialis and Echinocuccus spp., particularly preferably Taneiahydatigena, Taenia ovis, Taenia multiceps, Taenia serialis; Echinocuccusgranulosus and Echinotcoccus granulosus and Echinococcus multilocularis,and Multiceps multiceps.

In a very particularly preferred way, Taenia hydatigena, T. pisiformis,T. ovis, T. taeniaeformis, Multiceps multiceps, Joyeuxiella pasquali,Dipylidium caninum, Mesocestoides spp., Echinococcus granulosus and E.multilocularis are controlled simultaneously with Dirofilaria immitis,Ancylostoma spp., Toxocara spp. and/or Trichuris vulpis on or in dogsand cats. Also in a preferred way, Ctenocephalides felis and/or C. canisare controlled simultaneously with the abovementioned nematodes andcestodes.

The compounds of the formula I are also suitable for controllingparasites which are pathogenic to man, among which may be mentioned, astypical representatives occurring in the digestive tract, those of thegenera Ancylostoma, Necator, Ascaris, Strongyloides, Trichinella,Capillaria, Trichuris and Enterobius. The compounds of the presentinvention are also active against parasites of the genera Wuchereria,Brugia, Onchocerca and Loa from the family of the Filariidae, whichoccur in the blood, in tissue and in various organs, and also againstDracunculus and parasites of the genera Strongyloides and Trichinella,which specifically infect the gastrointestinal tract.

In addition, the compounds of the formula I are also active againstharmful fungi which cause disease in plants and in man and animals.

The good pesticidal action of the compounds of the formula I accordingto the invention corresponds to a kill rate (mortality) of at least50-60% of the pests mentioned. In particular, the compounds of theformula I are characterized by an extraordinarily long duration ofaction.

The compounds of the formula I are used as such or preferably togetherwith the auxiliaries conventional in formulation technology and canaccordingly be processed in a known way, for example to emulsifiableconcentrates, directly dilutable solutions, dilute emulsions, solublepowders, granules and also encapsulations in polymer substances. Theapplication methods as well as the compositions are chosen in accordancewith the intended aims and the prevailing circumstances.

The formulation, i.e. the compositions, preparations or combinationscomprising the active ingredient of the formula I, or combinations ofthese active ingredients with other active ingredients, and, if desired,a solid or liquid additive, is prepared in a known way, for example byintimately mixing and/or grinding the active ingredients with extenders,for example with solvents, solid carriers and, if desired,surface-active compounds (surfactants).

The following are possible as solvents: alcohols, such as ethanol,propanol or butanol, and glycols, and their ethers and esters, such aspropylene glycol, dipropylene glycol ether, ethylene glycol, ethyleneglycol monomethyl ether or ethylene glycol monoethyl ether, ketones,such as cyclohexanone, isophorone or diacetone alcohol, strongly polarsolvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide,dimethylformamide or water, vegetable oils, such as rapeseed oil, castoroil, coconut oil or soybean oil; and, if desired, silicone oils.

Preferred application forms for use in warm-blooded animals forcontrolling helminths include solutions, emulsions, suspensions(drenches), feed additives, powders, tablets, including effervescenttablets, boluses, capsules, microencapsulations and pour-onformulations, care having to be taken over the physiologicalcompatibility of the formulation auxiliaries.

Suitable binders for tablets and boluses are chemically modifiedpolymeric natural products which are soluble in water or alcohol, suchas starch, cellulose or protein derivatives (e.g., methylcellulose,carboxymethylcellulose, ethylhydroxyethylcellulose, proteins, such aszein, gelatin, and the like), and synthetic polymers, for examplepolyvinyl alcohol, polyvinylpyrrolidone, and the like. Tablets alsocomprise fillers (e.g., starch, microcrystalline cellulose, sugar,lactose, and the like), lubricants and disintegrating agents.

If the anthelmintic compositions are present in the form of feedconcentrates, then high-performance feed, feed cereals or proteinconcentrates, for example, are used as carriers. Such feed concentratesor compositions can, in addition to the active ingredients, alsocomprise additives, vitamins, antibiotics, chemotherapeutics, or otherpesticides, mainly bacteriostats, fungistats, coccidiostats, or alsohormone preparations, anabolics or substances which promote growth,influence the quality of meat from animals for slaughter or are usefulto the organism in another way. If the compositions or the activeingredients of the formula I present therein are added directly to thefeed or to the drinking water for the animals, the finished feed or thefinished drinking water comprises the active ingredients preferably in aconcentration from approximately 0.0005 to 0.02% by weight (5-200 ppm).

The compounds of the formula I according to the invention can be usedalone or in combination with other biocides. They can, e.g., be combinedwith pesticides possessing the same direction of action, in order toenhance the action, or can be combined with substances possessinganother direction of action, in order to broaden the activity spectrum.It may also make sense to add substances which repel, known asrepellents. If it is desired to expand the activity spectrum with regardto endoparasites, for example worms, the compounds of the formula I areappropriately combined with substances having endoparasiticidalproperties. They can also, naturally, be used in combination withantibacterial compositions. Since the compounds of the formula Irepresent adulticides, i.e. since they are effective in particularagainst the adult stages of the target parasites, the addition ofpesticides which are more likely to attack the juvenile stages ofparasites can be highly advantageous. In this way, most of thoseparasites causing great economic damage are namely included. Inaddition, a substantial contribution is also made as well to avoidingthe formation of resistance. Some combinations can also lead tosynergistic effects, i.e. that the total amount of active substanceconsumed can be reduced, which is desirable from an ecologicalviewpoint. Preferred groups of combination participants and particularlypreferred combination participants are mentioned subsequently, whichcombinations can, in addition to a compound of the formula I, compriseone or more of these participants.

Suitable participants in the mixture include biocides, for example theinsecticides and acaricides with different mechanisms of actionmentioned subsequently and sufficiently known to a person skilled in theart, for example chitin synthesis inhibitors, growth regulators; activeingredients which act as juvenile hormones; active ingredients which actas adulticides; broad spectrum insecticides, broad spectrum acaricidesand nematicides; but also the sufficiently known anthelmintics andsubstances which repel insects and/or members of the Acarina, known asrepellents or detachers.

Nonlimiting examples of suitable insecticides and acaricides are:  1.Abamectin  2. AC 303 630  3. Acephate  4. Acrinathrin  5. Alanycarb  6.Aldicarb  7. α-Cypermethrin  8. Alphamethrin  9. Amitraz  10. AvermectinB₁  11. AZ 60541  12. Azinphos E  13. Azinphos-methyl  14. Azocyclotin 15. Bacillus subtil. toxin  16. Bendiocarb  17. Benfuracarb  18.Bensultap  19. β-Cyfluthrin  20. Bifenthrin  21. BPMC  22. Brofenprox 23. Bromophos E  24. Bufencarb  25. Buprofezin  26. Butocarboxim  27.Butylpyridaben  28. Cadusafos  29. Carbaryl  30. Carbofuran  31.Carbophenothion  32. Cartap  33. Cloethocarb  34. Chlorethoxyfos  35.Chlorfenapyr  36. Chlorfluazuron  37. Chlormephos  38. Chlorpyrifos  39.Cis-Resmethrin  40. Clocythrin  41. Clofentezine  42. Cyanophos  43.Cycloprothrin  44. Cyfluthrin  45. Cyhexatin  46. D 2341  47.Deltamethrin  48. Demeton M  49. Demeton S  50. Demeton-S-methyl  51.Dibutylaminothio  52. Dichlofenthion  53. Dicliphos  54. Diethion  55.Diflubenzuron  56. Dimethoate  57. Dimethylvinphos  58. Dioxathion  59.DPX-MP062  60. Edifenphos  61. Emamectin  62. Endosulfan  63.Esfenvalerate  64. Ethiofencarb  65. Ethion  66. Ethofenprox  67.Ethoprophos  68. Etrimphos  69. Fenamiphos  70. Fenazaquin  71.Fenbutatin oxide  72. Fenitrothion  73. Fenobucarb  74. Fenothiocarb 75. Fenoxycarb  76. Fenpropathrin  77. Fenpyrad  78. Fenpyroximate  79.Fenthion  80. Fenvalerate  81. Fipronil  82. Fluazinam  83. Fluazuron 84. Flucycloxuron  85. Flucythrinate  86. Flufenoxuron  87. Flufenprox 88. Fonophos  89. Formothion  90. Fosthiazate  91. Fubfenprox  92. HCH 93. Heptenophos  94. Hexaflumuron  95. Hexythiazox  96. Hydroprene  97.Imidacloprid  98. Insect-active fungi  99. Insect-active     nematodes100. Insect-active     viruses 101. Iprobenfos 102. Isofenphos 103.Isoprocarb 104. Isoxathion 105. Ivermectin 106. λ-Cyhalothrin 107.Lufenuron 108. Malathion 109. Mecarbam 110. Mesulfenphos 111.Metaldehyde 112. Methamidophos 113. Methiocarb 114. Methomyl 115.Methoprene 116. Metolcarb 117. Mevinphos 118. Milbemectin 119.Moxidectin 120. Naled 121. NC 184 122. NI-25, Acetamiprid 123.Nitenpyram 124. Omethoate 125. Oxamyl 126. Oxydemeton M 127. Oxydeprofos128. Parathion 129. Parathion-methyl 130. Permethrin 131. Phenthoate132. Phorate 133. Phosalone 134. Phosmet 135. Phoxim 136. Pirimicarb137. Pirimiphos E 138. Pirimiphos M 139. Promecarb 140. Propaphos 141.Propoxur 142. Prothiofos 143. Prothoate 144. Pyraclophos 145.Pyradaphenthion 146. Pyresmethrin 147. Pyrethrum 148. Pyridaben 149.Pyrimidifen 150. Pyriproxyfen 151. RH-5992 152. RH-2485 153. Salithion154. Sebufos 155. Silafluofen 156. Spinosad 157. Sulfotep 158. Sulprofos159. Tebufenozide 160. Tebufenpyrad 161. Tebupirimphos 162.Teflubenzuron 163. Tefluthrin 164. Temephos 165. Terbam 166. Terbufos167. Tetrachlorvinphos 168. Thiafenox 169. Thiodicarb 170. Thiofanox171. Thionazin 172. Thuringiensin 173. Tralomethrin 174. Triarthene 175.Triazamate 176. Triazophos 177. Triazuron 178. Trichlorfon 179.Triflumuron 180. Trimethacarb 181. Vamidothion 182. XMC (3,5-xylyl    methylcarbamate) 183. Xylylcarb 184. YI 5301/5302 185. ζ-Cypermethrin186. Zetamethrin

Nonlimiting examples of suitable anthelmintics are mentionedsubsequently, in which some representatives, in addition to theanthelmintic activity, also have an insecticidal and acaricidal activityand are already included in the above list:

-   (A1)    Praziquantel=2-Cyclohexylcarbonyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-α]isoquinoline-   (A2)    Closantel=3,5-Diiodo-N-[5-chloro-2-methyl-4-(α-cyano-4-chlorobenzyl)phenyl]-salicylamide-   (A3)    Triclabendazole=5-Chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole-   (A4)    Levamisole=L-(−)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole-   (A5) Mebendazole=Methyl 5-benzoyl-1H-benzimidazol-2-ylcarbamate-   (A6) Omphalotin=a macrocyclic fermentation product from the fungus    Omphalotus olearius disclosed in WO 97/20857-   (A7) Abamectin=Avermectin B1-   (A8) Ivermectin=22,23-Dihydroavermectin B1-   (A9)    Moxidectin=5-O-Demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)milbemycin    B-   (A10)    Doramectin=25-Cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)avermectin    A1a-   (A11) Milbemectin=Mixture of Milbemycin A3 and Milbemycin A4-   (A12) Milbemycin oxime=5-Oxime of Milbemectin

Nonlimiting examples of suitable repelling substances (repellents ordetachers) are:

-   (R1) DEET (N,N-Diethyl-m-toluamide)-   (R2) KBR 3023 N-Butyl-2-oxycarbonyl-2-(2-hydroxyethyl)piperidine-   (R3)    Cymiazole=N-2,3-Dihydro-3-methyl-1,3-thiazol-2-ylidene-2,4-xylidine

The participants in the mixture which are mentioned are very well knownto a person skilled in the art. Most are described in the variouseditions of The Pesticide Manual, The British Crop Protection Council,London, others in the various editions of The Merck Index, Merck & Co.Inc., Rahway, N.J., USA, or in the patent literature. The followinglisting is accordingly restricted to a few references by way ofexamples.

-   (I) 2-Methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxime    (Aldicarb), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 26;-   (II) S-(3,4-Dihydro-4-oxobenzo[d][1,2,3]triazin-3-ylmethyl)    O,O-dimethyl phosphorodithioate-(Azinphos-methyl), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 67;-   (III) Ethyl    N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-β-alaninate    (Benfuracarb), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 96;-   (IV) 2-Methylbiphenyl-3-ylmethyl    (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate    (Bifenthrin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 118;-   (V) 2-tert-Butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one    (Buprofezin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 157;-   (VI) 2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamate    (Carbofuran), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 186;-   (VII)    2,3-Dihydro-2,2-dimethylbenzofuran-7-yl(dibutylaminothio)methylcarbamate    (Carbosulfan), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 188;-   (VIII) S,S′-(2-Dimethylaminotrimethylene)bis(thiocarbamate)    (Cartap), from The Pesticide Manual, 11^(th)Ed. (1997), The British    Crop Protection Council, London, page 193;-   (IX)    1-[3,5-Dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluorobenzoyl)-urea    (Chlorfluazuron), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 213;-   (X) O,O-Diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate    (Chlorpyrifos), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 235;-   (XI) (RS)-α-Cyano-4-fluoro-3-phenoxybenzyl(1RS,3RS;1    RS,3RS)-3-(2,2-dichlorovinyl)-2,2-di-methylcyclopropanecarboxylate    (Cyfluthrin), from The Pesticide Manual, 11^(th)Ed., (1997), The    British Crop Protection Council, London, page 293;-   (XII) Mixture of    (S)-α-cyano-3-phenoxybenzyl(2)-(1R,3R)-3-(2-chloro-3,3,3-trifluoro-propenyl)-2,2-dimethylcyclopropanecarboxylate    and    (R)-α-cyano-3-phenoxybenzyl(2)-(1S,3S)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate    (Lambda-Cyhalothrin), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 300;-   (XIII) Racemate consisting of    (S)-α-cyano-3-phenoxybenzyl(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    and    (R)-α-cyano-3-phenoxybenzyl(1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    (Alpha-cypermethrin), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 308;-   (XIV) A mixture of the stereoisomers of    (S)-α-cyano-3-phenoxybenzyl(1RS,3RS,1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    (zeta-Cypermethrin), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 314;-   (XV)    (S)-α-Cyano-3-phenoxybenzyl(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-carboxylate    (Deltamethrin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 344;-   (XVI) 1-(4-Chlorophenyl)-3-(2,6-difluorobenzoyl)urea    (Diflubenzuron), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 395;-   (XVII)    (1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-en-2,3-ylenebismethylene)sulfite    (Endosulfan), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 459;-   (XVIII) α-Ethylthio-o-tolyl methylcarbamate (Ethiofencarb), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 479;-   (XIX) O,O-Dimethyl O-4-nitro-m-tolyl phosphorothioate    (Fenitrothion), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 514;-   (XX) 2-sec-Butylphenyl methylcarbamate (Fenobucarb), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 516;-   (XXI)    (RS)-α-Cyano-3-phenoxybenzyl(RS)-2-(4-chlorophenyl)-3-methylbutyrate    (Fenvalerate), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 539;-   (XXII) S-[Formyl(methyl)carbamoylmethyl]O,O-dimethyl    phosphorodithioate (Formothion), from The Pesticide Manual,    11^(th)Ed. (1997), The British Crop Protection Council, London, page    625;-   (XXIII) 4-Methylthio-3,5-xylyl methylcarbamate (Methiocarb), from    The Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 813;-   (XXIV) 7-Chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl dimethyl phosphate    (Heptenophos), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 670;-   (XXV)    1-(6-Chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine    (Imidacloprid), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 706;-   (XXVI) 2-Isopropylphenyl methylcarbamate (Isoprocarb), from The    Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection    Council, London, page 729;-   (XXVII) O,S-Dimethyl phosphoramidothioate (Methamidophos), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 808;-   (XXVIII) S-Methyl N-(methylcarbamoyloxy)thioacetimidate (Methomyl),    from The Pesticide Manual, 11^(th)Ed. (1997), The British Crop    Protection Council, London, page 815;-   (XXIX) Methyl 3-(dimethoxyphosphinoyloxy)but-2-enoate (Mevinphos),    from The Pesticide Manual, 11^(th)Ed. (1997), The British Crop    Protection Council, London, page 844;-   (XXX) O,O-Diethyl O-4-nitrophenyl phosphorothioate (Parathion), from    The Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 926;-   (XXXI) O,O-Dimethyl O-4-nitrophenyl phosphorothioate    (Parathion-methyl), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 928;-   (XXXII) S-6-Chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl    O,O-diethyl phosphorodithioate (Phosalone), from The Pesticide    Manual, 11^(th)Ed. (1997), The British Crop Protection Council,    London, page 963;-   (XXXIII) 2-Dimethylamino-5,6-dimethylpyrimidin-4-yl    dimethylcarbamate (Pirimicarb), from The Pesticide Manual,    11^(th)Ed. (1997), The British Crop Protection Council, London, page    985;-   (XXXIV) 2-Isopropoxyphenyl methylcarbamate (Propoxur), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 1036;-   (XXXV)    1-(3,5-Dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea    (Teflubenzuron), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1158;-   (XXXVI) S-tert-Butylthiomethyl O,O-diethyl phosphorodithioate    (Terbufos), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1165;-   (XXXVII)    Ethyl(3-tert-butyl-1-dimethylcarbamoyl-1H-1,2,4-triazol-5-ylthio)acetate,    (Triazamate), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1224;-   (XXXVIII) Abamectin, from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 3;-   (XXXIX) 2-sec-Butylphenyl methylcarbamate (Fenobucarb), from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 516;-   (XL) N-tert-Butyl-N-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide    (Tebufenozide), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1147;-   (XLI)    (±)-5-Amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile    (Fipronil), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 545;-   (XLII) (RS)-α-Cyano-4-fluoro-3-phenoxybenzyl(1RS,3RS;1    RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    (beta-Cyfluthrin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 295;-   (XLIII)    (4-Ethoxyphenyl)[3-(4-fluoro-3-phenoxyphenyl)propyl](dimethyl)silane    (Silafluofen), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1105;-   (XLIV)    tert-Butyl(E)-α-(1,3-dimethyl-5-phenoxypyrazol-4-ylmethyleneamino-oxy)-p-toluate    (Fenpyroximate), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 530;-   (XLV)    2-tert-Butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2M-one    (Pyridaben), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1161;-   (XLVI) 4-[[4-(1,1-Dimethylethyl)phenyl]ethoxy]quinazoline    (Fenazaquin), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 507;-   (XLVII) 4-Phenoxyphenyl(RS)-2-(2-pyridyloxy)propyl ether    (Pyriproxyfen), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1073;-   (XLVIII)    5-Chloro-N-{2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethyl}-6-ethylpyrimidin-4-amine    (Pyrimidifen), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1070;-   (XLIX)    (E)-N-(6-Chloro-3-pyridylmethyl)-N-ethyl-V-methyl-2-nitrovinylidenediamine    (Nitenpyram), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 880;-   (L)    (E)-N¹-[(6-Chloro-3-pyridyl)methyl]-N²-cyano-N¹-methylacetamidine    (NI-25, Acetamiprid), from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 9;-   (LI) Avermectin B₁, from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 3;-   (LII) An insect-active extract from a plant, in particular    (2R,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno[3,4-b]furo[2,3-h]chromen-6-one    (Rotenone), from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 1097; and an extract    from Azadirachta indica, in particular azadirachtin, from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 59;-   (LIII) A preparation comprising insect-active nematodes, preferably    Heterorhabditis bacteriophora and Heterorhabditis megidis, from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 671; Steinernema feltiae, from The Pesticide    Manual, 11^(th)Ed. (1997), The British Crop Protection Council,    London, page 1115, and Steinernema scapterisci, from The Pesticide    Manual, 11^(th)Ed. (1997), The British Crop Protection Council,    London, page 1116;-   (LIV) A preparation obtainable from Bacillus subtilis, from The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 72; or from a Bacillus thunngiensis strain    except for compounds isolated from GC91 or from NCTC11821; The    Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection    Council, London, page 73;-   (LV) A preparation comprising insect-active fungi, preferably    Verticillium lecanil, from The Pesticide Manual, 11^(th)Ed. (1997),    The British Crop Protection Council, London, page 1266; Beauveda    brogniartii, from The Pesticide Manual, 11^(th)Ed. (1997), The    British Crop Protection Council, London, page 85; and Beauveda    bassiana, from The Pesticide Manual, 11^(th)Ed. (1997), The British    Crop Protection Council, London, page 83;-   (LVI) A preparation comprising insect-active viruses, preferably    Neodipridon Sertifer NPV, from The Pesticide Manual, 11^(th)Ed.    (1997), The British Crop Protection Council, London, page 1342;    Mamestra brassicae NPV, from The Pesticide Manual, 11^(th)Ed.    (1997), The British Crop Protection Council, London, page 759; and    Cydia pomonella granulosis virus, from The Pesticide Manual,    11^(th)Ed. (1997), The British Crop Protection Council, London, page    291;-   (CLXXXI) Methyl    7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxy-phenyl)carbamoyl]indol[1,2-e]oxazoline-4a-carboxylate    (DPX-MP062, Indoxacarb), from The Pesticide Manual, 11^(th)Ed.    (1997), The British Crop Protection Council, London, page 453;-   (CLXXXII)    N′-tert-Butyl-N′-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide    (RH-2485, Methoxyfenozide), from The Pesticide Manual, 11^(th)Ed.    (1997), The British Crop Protection Council, London, page 1094;-   (CLXXXIII) Isopropyl N′-[4-methoxybiphenyl-3-yl]hydrazinecarboxylate    (D 2341), from Brighton Crop Protection Conference, 1996, 487-493;    and-   (R2) Book of Abstracts, 212th ACS National Meeting, Orlando, Fla.,    Aug. 25-29 (1996), AGRO-020. Publisher: American Chemical Society,    Washington, D.C. CONEN: 63BFAF.

According to what has been said above, a further essential aspect of thepresent invention relates to combination preparations for the control ofparasites in warm-blooded animals, which comprise, in addition to acompound of the formula I, at least one further active ingredient withan identical or different direction of action and at least onephysiologically compatible carrier. The present invention is notrestricted to combinations of two.

The anthelmintic compositions according to the invention generallycomprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, ofactive ingredient of the formula I or mixtures thereof, and 99.9 to 1%by weight, in particular 99.8 to 5% by weight, of a solid or liquidadditive, including 0 to 25% by weight, in particular 0.1 to 25% byweight, of a surfactant.

The compositions according to the invention can be applied topically,perorally, parenterally or subcutaneously to the animals to be treated,the compositions being present in the form of solutions, emulsions,suspensions (drenches), powders, tablets, boluses, capsules and aspour-on formulations.

The pour-on or spot-oh method consists in applying the compound of theformula I to a locally restricted part of the skin or fur,advantageously on the neck or back of the animal. This is carried out,e.g., by applying a spot or dash of the pour-on or spot-on formulationto a relatively small area of the fur, from where the active substancespreads out virtually unaided over wide regions of the fur because ofthe spreading components of the formulation and supported by themovements of the animal.

It is advantageous for pour-on or spot-on formulations to comprisecarriers which promote speedy distribution on the surface of the skin orin the fur of the host animal and which are generally described asspreading oils. Suitable carriers are, e.g., oily solutions; alcoholicand isopropanolic solutions, for example solutions of 2-octyldodecanolor oleyl alcohol; solutions in esters of monocarboxylic acids, such asisopropyl myristate, isopropyl palmitate, lauric acid oxal ester, oleyloleate, decyl oleate, hexyl laurate, capric acid esters of saturatedfatty alcohols with a chain length of C₁₂-C₁₈; solutions of esters ofdicarboxylic acids, such as dibutyl phthalate, diisopropyl isophthalate,diisopropyl adipate or di(n-butyl) adipate, or also solutions of estersof aliphatic acids, e.g. glycols. It can be advantageous if a dispersantknown from the pharmaceutical or cosmetics industry is additionallypresent. Examples are 2-pyrrolidone, 2-(N-alkyl)pyrrolidone, acetone,polyethylene glycol and ethers and esters thereof, propylene glycol orsynthetic triglycerides.

The oily solutions include, e.g., vegetable oils, such as olive oil,groundnut oil, sesame oil, pine oil, linseed oil or castor oil. Thevegetable oils can also be present in epoxidized form. Paraffin oils andsilicone oils can also be used.

In general, a pour-on or spot-on formulation comprises 1 to 20% byweight of a compound of the formula I, 0.1 to 50% by weight ofdispersant and 45 to 98.9% by weight of solvent.

The pour-on or spot-on method can be used particularly advantageouslywith gregarious animals, such as cattle, horses, sheep or pigs, where itis difficult or time-consuming to treat all the animals orally or viainjection. Because of its simplicity, this method can naturally also beused with all other animals, including individual domestic animals orpets, and is very popular with animal owners because it can often beimplemented without the expert assistance of a veterinary surgeon.

While concentrated compositions are more preferred as commerciallyavailable products, the end user generally uses dilute compositions.

Such compositions can comprise yet further additives, such asstabilizers, antifoaming agents, viscosity regulators, binders, depositbuilders and other active ingredients to obtain specific effects.

Such anthelmintic compositions used by the end user likewise form partof the present invention.

In each of the methods according to the invention for controlling pestsor of the pesticides according to the invention, the active ingredientsof the formula I can be used in all their steric configurations ormixtures thereof.

The invention also includes a method for the prophylactic protection ofwarm-blooded animals, in particular of productive livestock, domesticanimals and pets, against parasitic helminths, which comprises applyingthe active ingredients of the formula I or the active ingredientformulations prepared therefrom as a feed additive or drinking wateradditive or also in the solid or liquid form, orally, by injection orparenterally, to the animals. The invention also includes the compoundsof the formula I according to the invention for use in one of themethods mentioned.

The following examples serve merely to illustrate the invention, withoutlimiting it, the term “active ingredient” representing a substancelisted in Table 1.

Preferred formulations are in particular composed in the following way:

(%=percent by weight)

FORMULATION EXAMPLES

1. Granules a) b) Active ingredient  5% 10% Kaolin 94% — Highlydispersed silica  1% — Attapulgite — 90%

The active ingredient is dissolved in methylene chloride and sprayedonto the carrier, and the solvent is subsequently evaporated underreduced pressure. Such granules can be added to the animal feed. 2.Granules Active ingredient 3% Polyethylene glycol (MW 200) 3% Kaolin 94%(MW = molecular weight)

The finely milled active ingredient is applied evenly in a mixer to thekaolin, which has been moistened with polyethylene glycol. In this way,dust-free coated granules are obtained. 3. Tablets or Boluses I Activeingredient 33.00% Methylcellulose 0.80% Highly dispersed silica 0.80%Maize starch 8.40% II Cryst. lactose 22.50% Maize starch 17.00%Microcryst. cellulose 16.50% Magnesium stearate 1.00%

-   I Methylcellulose is stirred into water. After the material has    swollen, silica is stirred in and the mixture is homogeneously    suspended. Active ingredient and maize starch are mixed. The aqueous    suspension is incorporated in this mixture and kneaded to a dough.    The substance thus obtained is granulated through a 12 M sieve and    dried.-   II All 4 auxiliaries are intimately mixed.

III The premixes obtained according to I and II are mixed and pressed togive tablets or boluses. 4. Injectables A. Oily vehicle (slowrelease) 1. Active ingredient 0.1-1.0 g Groundnut oil ad 100 ml 2.Active ingredient 0.1-1.0 g Sesame oil ad 100 ml

Preparation: The active ingredient is dissolved in a portion of the oilwith stirring and, if desired, gentle heating, made up to the requiredvolume after cooling and sterilely filtered through a suitable membranefilter with a size of 0.22 μm. B. Water-miscible solvent (medium releaserate) 1. Active ingredient 0.1-1.0 g 4-Hydroxymethyl-1,3-dioxolane(glycerol formal) 40 g 1,2-Propanediol ad 100 ml 2. Active ingredient0.1-1.0 g Glycerol dimethyl acetal 40 g 1,2-Propanediol ad 100 ml

Preparation: The active ingredient is dissolved in a portion of thesolvent with stirring, made up to the required volume and sterilelyfiltered through a suitable membrane filter with a size of 0.22 μm. C.Aqueous solubilisate (rapid release) 1. Active ingredient 0.1-1.0 gPolyethoxylated castor oil (40 ethylene oxide units) 10 g1,2-Propanediol 20 g Benzyl alcohol 1 g Water for injections ad 100 ml2. Active ingredient 0.1-1.0 g Polyethoxylated sorbitan monooleate 8 g(20 ethylene oxide units) 4-Hydroxymethyl-1,3-dioxolane (glycerolformal) 20 g Benzyl alcohol 1 g Water for injections ad 100 ml

Preparation: The active ingredient is dissolved in the solvents and thesurfactant and made up to the required volume with water. Sterilefiltration is carried out through a suitable membrane filter with a porediameter of 0.22 μm. 5. Pour-on A. Active ingredient 5 g Isopropylmyristate 10 g Isopropanol ad 100 ml B. Active ingredient 2 g Hexyllaurate 5 g Triglycerides of medium chain length 15 g Ethanol ad 100 mlC. Active ingredient 2 g Oleyl oleate 5 g N-Methylpyrrolidone 40 gIsopropanol ad 100 ml

The aqueous systems can preferably also be used for oral and/orintraruminal administration.

The compositions can also comprise further additives, such asstabilizers, e.g. epoxidized or nonepoxidized vegetable oils (epoxidizedcoconut oil, rapeseed oil or soybean oil), antifoaming agents, e.g.silicone oil, preservatives, viscosity regulators, binders, depositbuilders and fertilizers or other active ingredients to obtain specificeffects.

Further biologically active substances or additives which are neutraltowards the compounds of the formula I and have no adverse effect on thehost animal to be treated, and mineral salts or vitamins, can also beadded to the compositions described.

The following examples serve to clarify the invention. They do not limitthe invention. The symbol ‘h’ denotes hour.

PREPARATION EXAMPLES Example 1 4-(2-Trifluoromethylphenyl)-3-buten-2-one

a) 4.29 g of N,O-dimethylhydroxylamine hydrochloride, 9.5 g of2-trifluoromethylcinnamic acid, 11.36 g of ethyldiisopropylamine, 0.45 gof 4-dimethylaminopyridine and 8.43 g ofN-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride aredissolved in 80 ml of methylene chloride and are stirred at ambienttemperature under a nitrogen atmosphere for 8 h. The mixture issubsequently diluted with 200 ml of ethyl acetate and then washed twicewith 1 N hydrochloric acid solution, then twice with a saturated sodiumbicarbonate solution and finally once with saturated sodium chloridesolution. The organic phase is separated, dried with magnesium sulfateand evaporated under reduced pressure. After purifying by flashchromatography, N-methoxy-N-methyl-3-(2-trifluoromethylphenyl)acrylamideIs thus obtained.

b) 11 g of N-methoxy-N-methyl-3-(2-trifluoromethylphenyl)acrylamide aredissolved in 150 ml of dry tetrahydrofuran under a nitrogen atmosphere,cooled to −78° C. and treated dropwise with 36 ml of a 1.4N solution ofmethyllithium in diethyl ether in 10 minutes. The solution issubsequently furthermore stirred at −78° C. for 2 h and then hydrolysedwith water. 200 ml of ethyl acetate are now added at ambient temperatureand the mixture is washed three times with saturated sodium chloridesolution. The organic phase is finally separated, dried with magnesiumsulfate and evaporated under reduced pressure. After purifying by flashchromatography, the title compound is thus obtained.

Example 2 4-(2-Trifluoromethylphenyl)butan-2-one

200 mg of Raney nickel are added to a solution of 2.05 g of4-(2-trifluoromethylphenyl)-3-buten-2-one in 100 ml of ethyl acetate andthe mixture is stirred under a hydrogen atmosphere and at standardpressure for 7 h. The mixture is subsequently filtered and the filtrateis evaporated under reduced pressure, whereby the title compound isobtained.

Example 3 2-Amino-2-methyl-4-(2-trifluoromethylphenyl)butyronitrile

1.5 g of 4-(2-trifluoromethylphenyl)butan-2-one, 0.41 g of sodiumcyanide and 0.56 g of ammonium chloride are dissolved in 77 ml of a 2Msolution of ammonia in ethanol and the mixture is stirred at ambienttemperature for 7 h. The mixture is subsequently concentrated underreduced pressure and the residue is redissolved in ethyl acetate andwashed with water and three times with saturated sodium chloridesolution. The organic phase is separated, dried with magnesium sulfateand evaporated under reduced pressure. After purifying the residue byflash chromatography, the title compound is thus obtained.

Example 4N-(1-cyano-1-methyl-3-[2-trifluoromethylphenyl]propyl)-4-trifluoromethoxy-benzamide

200 mg of 2-amino-2-methyl-4-(2-trifluoromethylphenyl)butyronitrile, 185mg of 4-trifluoro-methoxybenzoyl chloride, 107 mg ofethyldiisopropylamine and 10 mg of 4-dimethylamino-pyridine aredissolved in 10 ml of methylene chloride and the mixture is stirredunder a nitrogen atmosphere for 6 h. After the addition of 50 ml ofethyl acetate, the organic phase is washed once with water and thentwice with saturated sodium chloride solution. The organic phase isseparated, dried with magnesium sulfate and evaporated under reducedpressure. After purifying the residue by flash chromatography, the titlecompound is thus obtained as white crystals with a melting point of87-9° C.

The substances mentioned in the following table can also be preparedanalogously to the procedure described above. The melting point valuesare given in ° C. TABLE 1

No. X R₉ R₁₀ Phys. data 1.1 CH₂CH₂ H H 1.2 CH₂CH₂ H 2-F 1.3 CH₂CH₂ H 3-F1.4 CH₂CH₂ H 4-F 1.5 CH₂CH₂ H 2-Cl 1.6 CH₂CH₂ H 3-Cl 1.7 CH₂CH₂ H 4-Cl1.8 CH₂CH₂ H 2-CH₃ 1.9 CH₂CH₂ H 3-CH₃ 1.10 CH₂CH₂ H 4-CH₃ 1.11 CH₂CH₂ H2-CF₃ 1.12 CH₂CH₂ H 3-CF₃ 1.13 CH₂CH₂ H 4-CF₃ 1.14 CH₂CH₂ H 2-OCF₃ 1.15CH₂CH₂ H 3-OCF₃ 1.16 CH₂CH₂ H 4-OCF₃ M.p. 129° C. 1.17 CH₂CH₂ H2-OCF₂CF₂H 1.18 CH₂CH₂ H 3-OCF₂CF₂H 1.19 CH₂CH₂ H 4-OCF₂CF₂H 1.20 CH₂CH₂H 2-OCF₂CF₃ 1.21 CH₂CH₂ H 3-OCF₂CF₃ 1.22 CH₂CH₂ H 4-OCF₂CF₃ 1.23 CH₂CH₂H 2-OC₆H₅ 1.24 CH₂CH₂ H 3-OC₆H₅ 1.25 CH₂CH₂ H 4-OC₆H₅ 1.26 CH₂CH₂ H2-NHC₆H₅ 1.27 CH₂CH₂ H 3-NHC₆H₅ 1.28 CH₂CH₂ H 4-NHC₆H₅ 1.29 CH₂CH₂ H2-NCH₃C₆H₅ 1.30 CH₂CH₂ H 3-NCH₃C₆H₅ 1.31 CH₂CH₂ H 4-NCH₃C₆H₅ 1.32 CH₂CH₂H 2-C(O)C₆H₅ 1.33 CH₂CH₂ H 3-C(O)C₆H₅ 1.34 CH₂CH₂ H 4-C(O)C₆H₅ 1.35CH₂CH₂ H 2-C(NOCH₃)C₆H₅ 1.36 CH₂CH₂ H 3-C(NOCH₃)C₆H₅ 1.37 CH₂CH₂ H4-C(NOCH₃)C₆H₅ 1.38 CH₂CH₂ H 2-CH(CN)C₆H₅ 1.39 CH₂CH₂ H 3-CH(CN)C₆H₅1.40 CH₂CH₂ H 4-CH(CN)C₆H₅ 1.41 CH₂CH₂ 2-F H 1.42 CH₂CH₂ 2-F 2-F 1.43CH₂CH₂ 2-F 3-F 1.44 CH₂CH₂ 2-F 4-F 1.45 CH₂CH₂ 2-F 2-Cl 1.46 CH₂CH₂ 2-F3-Cl 1.47 CH₂CH₂ 2-F 4-Cl 1.48 CH₂CH₂ 2-F 2-CH₃ 1.49 CH₂CH₂ 2-F 3-CH₃1.50 CH₂CH₂ 2-F 4-CH₃ 1.51 CH₂CH₂ 2-F 2-CF₃ 1.52 CH₂CH₂ 2-F 3-CF₃ 1.53CH₂CH₂ 2-F 4-CF₃ 1.54 CH₂CH₂ 2-F 2-OCF₃ 1.55 CH₂CH₂ 2-F 3-OCF₃ 1.56CH₂CH₂ 2-F 4-OCF₃ 1.57 CH₂CH₂ 2-F 2-OCF₂CF₂H 1.58 CH₂CH₂ 2-F 3-OCF₂CF₂H1.59 CH₂CH₂ 2-F 4-OCF₂CF₂H 1.60 CH₂CH₂ 2-F 2-OCF₂CF₃ 1.61 CH₂CH₂ 2-F3-OCF₂CF₃ 1.62 CH₂CH₂ 2-F 4-OCF₂CF₃ 1.63 CH₂CH₂ 2-F 2-OC₆H₅ 1.64 CH₂CH₂2-F 3-OC₆H₅ 1.65 CH₂CH₂ 2-F 4-OC₆H₅ 1.66 CH₂CH₂ 2-F 2-NHC₆H₅ 1.67 CH₂CH₂2-F 3-NHC₆H₅ 1.68 CH₂CH₂ 2-F 4-NHC₆H₅ 1.69 CH₂CH₂ 2-F 2-NCH₃C₆H₅ 1.70CH₂CH₂ 2-F 3-NCH₃C₆H₅ 1.71 CH₂CH₂ 2-F 4-NCH₃C₆H₅ 1.72 CH₂CH₂ 2-F2-C(O)C₆H₅ 1.73 CH₂CH₂ 2-F 3-C(O)C₆H₅ 1.74 CH₂CH₂ 2-F 4-C(O)C₆H₅ 1.75CH₂CH₂ 2-F 2-C(NOCH₃)C₆H₅ 1.76 CH₂CH₂ 2-F 3-C(NOCH₃)C₆H₅ M.p. 87-9° 1.77CH₂CH₂ 2-F 4-C(NOCH₃)C₆H₅ 1.78 CH₂CH₂ 2-F 2-CH(CN)C₆H₅ 1.79 CH₂CH₂ 2-F3-CH(CN)C₆H₅ viscous oil 1.80 CH₂CH₂ 2-F 4-CH(CN)C₆H₅ 1.81 CH₂CH₂ 3-F H1.82 CH₂CH₂ 3-F 2-F 1.83 CH₂CH₂ 3-F 3-F 1.84 CH₂CH₂ 3-F 4-F 1.85 CH₂CH₂3-F 2-Cl 1.86 CH₂CH₂ 3-F 3-Cl 1.87 CH₂CH₂ 3-F 4-Cl 1.88 CH₂CH₂ 3-F 2-CH₃1.89 CH₂CH₂ 3-F 3-CH₃ 1.90 CH₂CH₂ 3-F 4-CH₃ 1.91 CH₂CH₂ 3-F 2-CF₃ 1.92CH₂CH₂ 3-F 3-CF₃ 1.93 CH₂CH₂ 3-F 4-CF₃ 1.94 CH₂CH₂ 3-F 2-OCF₃ M.p.99-101° 1.95 CH₂CH₂ 3-F 3-OCF₃ 1.96 CH₂CH₂ 3-F 4-OCF₃ 1.97 CH₂CH₂ 3-F2-OCF₂CF₂H 1.98 CH₂CH₂ 3-F 3-OCF₂CF₂H 1.99 CH₂CH₂ 3-F 4-OCF₂CF₂H 1.100CH₂CH₂ 3-F 2-OCF₂CF₃ 1.101 CH₂CH₂ 3-F 3-OCF₂CF₃ 1.102 CH₂CH₂ 3-F4-OCF₂CF₃ 1.103 CH₂CH₂ 3-F 2-OC₆H₅ 1.104 CH₂CH₂ 3-F 3-OC₆H₅ 1.105 CH₂CH₂3-F 4-OC₆H₅ 1.106 CH₂CH₂ 3-F 2-NHC₆H₅ 1.107 CH₂CH₂ 3-F 3-NHC₆H₅ 1.108CH₂CH₂ 3-F 4-NHC₆H₅ 1.109 CH₂CH₂ 3-F 2-NCH₃C₆H₅ 1.110 CH₂CH₂ 3-F3-NCH₃C₆H₅ 1.111 CH₂CH₂ 3-F 4-NCH₃C₆H₅ 1.112 CH₂CH₂ 3-F 2-C(O)C₆H₅ 1.113CH₂CH₂ 3-F 3-C(O)C₆H₅ 1.114 CH₂CH₂ 3-F 4-C(O)C₆H₅ 1.115 CH₂CH₂ 3-F2-C(NOCH₃)C₆H₅ 1.116 CH₂CH₂ 3-F 3-C(NOCH₃)C₆H₅ 1.117 CH₂CH₂ 3-F4-C(NOCH₃)C₆H₅ 1.118 CH₂CH₂ 3-F 2-CH(CN)C₆H₅ 1.119 CH₂CH₂ 3-F3-CH(CN)C₆H₅ 1.120 CH₂CH₂ 3-F 4-CH(CN)C₆H₅ 1.121 CH₂CH₂ 4-F H 1.122CH₂CH₂ 4-F 2-F 1.123 CH₂CH₂ 4-F 3-F 1.124 CH₂CH₂ 4-F 4-F 1.125 CH₂CH₂4-F 2-Cl 1.126 CH₂CH₂ 4-F 3-Cl 1.127 CH₂CH₂ 4-F 4-Cl 1.128 CH₂CH₂ 4-F2-CH₃ 1.129 CH₂CH₂ 4-F 3-CH₃ 1.130 CH₂CH₂ 4-F 4-CH₃ 1.131 CH₂CH₂ 4-F2-CF₃ 1.132 CH₂CH₂ 4-F 3-CF₃ 1.133 CH₂CH₂ 4-F 4-CF₃ 1.134 CH₂CH₂ 4-F2-OCF₃ 1.135 CH₂CH₂ 4-F 3-OCF₃ 1.136 CH₂CH₂ 4-F 4-OCF₃ 1.137 CH₂CH₂ 4-F2-OCF₂CF₂H 1.138 CH₂CH₂ 4-F 3-OCF₂CF₂H 1.139 CH₂CH₂ 4-F 4-OCF₂CF₂H 1.140CH₂CH₂ 4-F 2-OCF₂CF₃ 1.141 CH₂CH₂ 4-F 3-OCF₂CF₃ 1.142 CH₂CH₂ 4-F4-OCF₂CF₃ 1.143 CH₂CH₂ 4-F 2-OC₆H₅ 1.144 CH₂CH₂ 4-F 3-OC₆H₅ 1.145 CH₂CH₂4-F 4-OC₆H₅ 1.146 CH₂CH₂ 4-F 2-NHC₆H₅ 1.147 CH₂CH₂ 4-F 3-NHC₆H₅ 1.148CH₂CH₂ 4-F 4-NHC₆H₅ 1.149 CH₂CH₂ 4-F 2-NCH₃C₆H₅ 1.150 CH₂CH₂ 4-F3-NCH₃C₆H₅ 1.151 CH₂CH₂ 4-F 4-NCH₃C₆H₅ 1.152 CH₂CH₂ 4-F 2-C(O)C₆H₅ 1.153CH₂CH₂ 4-F 3-C(O)C₆H₅ 1.154 CH₂CH₂ 4-F 4-C(O)C₆H₅ 1.155 CH₂CH₂ 4-F2-C(NOCH₃)C₆H₅ 1.156 CH₂CH₂ 4-F 3-C(NOCH₃)C₆H₅ 1.157 CH₂CH₂ 4-F4-C(NOCH₃)C₆H₅ 1.158 CH₂CH₂ 4-F 2-CH(CN)C₆H₅ 1.159 CH₂CH₂ 4-F3-CH(CN)C₆H₅ 1.160 CH₂CH₂ 4-F 4-CH(CN)C₆H₅ 1.161 CH₂CH₂ 2-CF₃ H 1.162CH₂CH₂ 2-CF₃ 2-F 1.163 CH₂CH₂ 2-CF₃ 3-F 1.164 CH₂CH₂ 2-CF₃ 4-F 1.165CH₂CH₂ 2-CF₃ 2-Cl 1.166 CH₂CH₂ 2-CF₃ 3-Cl 1.167 CH₂CH₂ 2-CF₃ 4-Cl 1.168CH₂CH₂ 2-CF₃ 2-CH₃ 1.169 CH₂CH₂ 2-CF₃ 3-CH₃ 1.170 CH₂CH₂ 2-CF₃ 4-CH₃1.171 CH₂CH₂ 2-CF₃ 2-CF₃ 1.172 CH₂CH₂ 2-CF₃ 3-CF₃ 1.173 CH₂CH₂ 2-CF₃4-CF₃ 1.174 CH₂CH₂ 2-CF₃ 2-OCF₃ 1.175 CH₂CH₂ 2-CF₃ 3-OCF₃ 1.176 CH₂CH₂2-CF₃ 4-OCF₃ M.p. 87~9o 1.177 CH₂CH₂ 2-CF₃ 2-OCF₂CF₂H 1.178 CH₂CH₂ 2-CF₃3-OCF₂CF₂H 1.179 CH₂CH₂ 2-CF₃ 4-OCF₂CF₂H viscous oil 1.180 CH₂CH₂ 2-CF₃2-OCF₂CF₃ 1.181 CH₂CH₂ 2-CF₃ 3-OCF₂CF₃ 1.182 CH₂CH₂ 2-CF₃ 4-OCF₂CF₃1.183 CH₂CH₂ 2-CF₃ 2-OC₆H₅ 1.184 CH₂CH₂ 2-CF₃ 3-OC₆H₅ 1.185 CH₂CH₂ 2-CF₃4-OC₆H₅ 1.186 CH₂CH₂ 2-CF₃ 2-NHC₆H₅ 1.187 CH₂CH₂ 2-CF₃ 3-NHC₆H₅ 1.188CH₂CH₂ 2-CF₃ 4-NHC₆H₅ 1.189 CH₂CH₂ 2-CF₃ 2-NCH₃C₆H₅ 1.190 CH₂CH₂ 2-CF₃3-NCH₃C₆H₅ 1.191 CH₂CH₂ 2-CF₃ 4-NCH₃C₆H₅ 1.192 CH₂CH₂ 2-CF₃ 2-C(O)C₆H₅1.193 CH₂CH₂ 2-CF₃ 3-C(O)C₆H₅ 1.194 CH₂CH₂ 2-CF₃ 4-C(O)C₆H₅ M.p. 99~1010 1.195 CH₂CH₂ 2-CF₃ 2-C(NOCH₃)C₆H₅ 1.196 CH₂CH₂ 2-CF₃ 3-C(NOCH₃)C₆H₅1.197 CH₂CH₂ 2-CF₃ 4-C(NOCH₃)C₆H₅ 1.198 CH₂CH₂ 2-CF₃ 2-CH(CN)C₆H₅ 1.199CH₂CH₂ 2-CF₃ 3-CH(CN)C₆H₅ 1.200 CH₂CH₂ 2-CF₃ 4-CH(CN)C₆H₅ 1.201 CH₂CH₂3-CF₃ H 1.202 CH₂CH₂ 3-CF₃ 2-F 1.203 CH₂CH₂ 3-CF₃ 3-F 1.204 CH₂CH₂ 3-CF₃4-F 1.205 CH₂CH₂ 3-CF₃ 2-Cl 1.206 CH₂CH₂ 3-CF₃ 3-Cl 1.207 CH₂CH₂ 3-CF₃4-Cl 1.208 CH₂CH₂ 3-CF₃ 2-CH₃ 1.209 CH₂CH₂ 3-CF₃ 3-CH₃ 1.210 CH₂CH₂3-CF₃ 4-CH₃ 1.211 CH₂CH₂ 3-CF₃ 2-CF₃ 1.212 CH₂CH₂ 3-CF₃ 3-CF₃ 1.213CH₂CH₂ 3-CF₃ 4-CF₃ 1.214 CH₂CH₂ 3-CF₃ 2-OCF₃ 1.215 CH₂CH₂ 3-CF₃ 3-OCF₃1.216 CH₂CH₂ 3-CF₃ 4-OCF₃ 1.217 CH₂CH₂ 3-CF₃ 2-OCF₂CF₂H 1.218 CH₂CH₂3-CF₃ 3-OCF₂CF₂H 1.219 CH₂CH₂ 3-CF₃ 4-OCF₂CF₂H 1.220 CH₂CH₂ 3-CF₃2-OCF₂CF₃ 1.221 CH₂CH₂ 3-CF₃ 3-OCF₂CF₃ 1.222 CH₂CH₂ 3-CF₃ 4-OCF₂CF₃1.223 CH₂CH₂ 3-CF₃ 2-OC₆H₅ 1.224 CH₂CH₂ 3-CF₃ 3-OC₆H₅ 1.225 CH₂CH₂ 3-CF₃4-OC₆H₅ 1.226 CH₂CH₂ 3-CF₃ 2-NHC₆H₅ 1.227 CH₂CH₂ 3-CF₃ 3-NHC₆H₅ 1.228CH₂CH₂ 3-CF₃ 4-NHC₆H₅ 1.229 CH₂CH₂ 3-CF₃ 2-NCH₃C₆H₅ 1.230 CH₂CH₂ 3-CF₃3-NCH₃C₆H₅ 1.231 CH₂CH₂ 3-CF₃ 4-NCH₃C₆H₅ 1.232 CH₂CH₂ 3-CF₃ 2-C(O)C₆H₅1.233 CH₂CH₂ 3-CF₃ 3-C(O)C₆H₅ 1.234 CH₂CH₂ 3-CF₃ 4-C(O)C₆H₅ 1.235 CH₂CH₂3-CF₃ 2-C(NOCH₃)C₆H₅ 1.236 CH₂CH₂ 3-CF₃ 3-C(NOCH₃)C₆H₅ 1.237 CH₂CH₂3-CF₃ 4-C(NOCH₃)C₆H₅ 1.238 CH₂CH₂ 3-CF₃ 2-CH(CN)C₆H₅ 1.239 CH₂CH₂ 3-CF₃3-CH(CN)C₆H₅ 1.240 CH₂CH₂ 3-CF₃ 4-CH(CN)C₆H₅ 1.241 CH₂CH₂ 4-CF₃ H 1.242CH₂CH₂ 4-CF₃ 2-F 1.243 CH₂CH₂ 4-CF₃ 3-F 1.244 CH₂CH₂ 4-CF₃ 4-F 1.245CH₂CH₂ 4-CF₃ 2-Cl 1.246 CH₂CH₂ 4-CF₃ 3-Cl 1.247 CH₂CH₂ 4-CF₃ 4-Cl 1.248CH₂CH₂ 4-CF₃ 2-CH₃ 1.249 CH₂CH₂ 4-CF₃ 3-CH₃ 1.250 CH₂CH₂ 4-CF₃ 4-CH₃1.251 CH₂CH₂ 4-CF₃ 2-CF₃ 1.252 CH₂CH₂ 4-CF₃ 3-CF₃ 1.253 CH₂CH₂ 4-CF₃4-CF₃ 1.254 CH₂CH₂ 4-CF₃ 2-OCF₃ 1.255 CH₂CH₂ 4-CF₃ 3-OCF₃ 1.256 CH₂CH₂4-CF₃ 4-OCF₃ 1.257 CH₂CH₂ 4-CF₃ 2-OCF₂CF₂H 1.258 CH₂CH₂ 4-CF₃ 3-OCF₂CF₂H1.259 CH₂CH₂ 4-CF₃ 4-OCF₂CF₂H 1.260 CH₂CH₂ 4-CF₃ 2-OCF₂CF₃ 1.261 CH₂CH₂4-CF₃ 3-OCF₂CF₃ 1.262 CH₂CH₂ 4-CF₃ 4-OCF₂CF₃ 1.263 CH₂CH₂ 4-CF₃ 2-OC₆H₅1.264 CH₂CH₂ 4-CF₃ 3-OC₆H₅ 1.265 CH₂CH₂ 4-CF₃ 4-OC₆H₅ 1.266 CH₂CH₂ 4-CF₃2-NHC₆H₅ 1.267 CH₂CH₂ 4-CF₃ 3-NHC₆H₅ 1.268 CH₂CH₂ 4-CF₃ 4-NHC₆H₅ 1.269CH₂CH₂ 4-CF₃ 2-NCH₃C₆H₅ 1.270 CH₂CH₂ 4-CF₃ 3-NCH₃C₆H₅ 1.271 CH₂CH₂ 4-CF₃4-NCH₃C₆H₅ 1.272 CH₂CH₂ 4-CF₃ 2-C(O)C₆H₅ 1.273 CH₂CH₂ 4-CF₃ 3-C(O)C₆H₅1.274 CH₂CH₂ 4-CF₃ 4-C(O)C₆H₅ 1.275 CH₂CH₂ 4-CF₃ 2-C(NOCH₃)C₆H₅ 1.276CH₂CH₂ 4-CF₃ 3-C(NOCH₃)C₆H₅ 1.277 CH₂CH₂ 4-CF₃ 4-C(NOCH₃)C₆H₅ 1.278CH₂CH₂ 4-CF₃ 2-CH(CN)C₆H₅ 1.279 CH₂CH₂ 4-CF₃ 3-CH(CN)C₆H₅ 1.280 CH₂CH₂4-CF₃ 4-CH(CN)C₆H₅ 1.281 CH₂CH₂ 4-OCH₃ 4-OCF₃ M.p. 125° 1.282 CH₂CH₂2-CF₃, 4,5-F₂ H 1.283 CH₂CH₂ 2-CF₃, 4,5-F₂ 2-F 1.284 CH₂CH₂ 2-CF₃,4,5-F₂ 3-F 1.285 CH₂CH₂ 2-CF₃, 4,5-F₂ 4-F 1.286 CH₂CH₂ 2-CF₃, 4,5-F₂2-Cl 1.287 CH₂CH₂ 2-CF₃, 4,5-F₂ 3-Cl 1.288 CH₂CH₂ 2-CF₃, 4,5-F₂ 4-Cl1.289 CH₂CH₂ 2-CF₃, 4,5-F₂ 2-CH₃ 1.290 CH₂CH₂ 2-CF₃, 4,5-F₂ 3-CH₃ 1.291CH₂CH₂ 2-CF₃, 4,5-F₂ 4-CH₃ 1.292 CH₂CH₂ 2-CF₃, 4,5-F₂ 2-CF₃ 1.293 CH₂CH₂2-CF₃, 4,5-F₂ 3-CF₃ 1.294 CH₂CH₂ 2-CF₃, 4,5-F₂ 4-CF₃ 1.295 CH₂CH₂ 2-CE₃,4,5-F₂ 2-OCF₃ 1.296 CH₂CH₂ 2-CF₃, 4,5-F₂ 3-OCF₃ 1.297 CH₂CH₂ 2-CF₃,4,5-F₂ 4-OCF₃ 1.298 CH₂CH₂ 2-CF₃, 4,5-F₂ 2-OCF₂CF₂H 1.299 CH₂CH₂ 2-CF₃,4,5-F₂ 3-OCF₂CF₂H 1.300 CH₂CH₂ 2-CF₃, 4,5-F₂ 4-OCF₂CF₂H 1.301 CH₂CH₂2-CF₃, 4,5-F₂ 2-OCF₂CF₃ 1.302 CH₂CH₂ 2-CF₃, 4,5-F₂ 3-OCF₂CF₃ 1.303CH₂CH₂ 2-CF₃, 4,5-F₂ 4-OCF₂CF₃ 1.304 CH₂CH₂ 2-CF₃, 4,5-F₂ 2-OC₆H₅ 1.305CH₂CH₂ 2-CF₃, 4,5-F₂ 3-OC₆H₅ 1.306 CH₂CH₂ 2-CF₃, 4,5-F₂ 4-OC₆H₅ 1.307CH₂CH₂ 2-CF₃, 4,5-F₂ 2-NHC₆H₅ 1.308 CH₂CH₂ 2-CF₃, 4,5-F₂ 3-NHC₆H₅ 1.309CH₂CH₂ 2-CF₃, 4,5-F₂ 4-NHC₆H₅ 1.310 CH₂CH₂ 2-CF₃, 4,5-F₂ 2-NCH₃C₆H₅1.311 CH₂CH₂ 2-CF₃, 4,5-F₂ 3-NCH₃C₆H₅ 1.312 CH₂CH₂ 2-CF₃, 4,5-F₂4-NCH₃C₆H₅ 1.313 CH₂CH₂ 2-CF₃, 4,5-F₂ 2-C(O)C₆H₅ 1.314 CH₂CH₂ 2-CF₃,4,5-F₂ 3-C(O)C₆H₅ 1.315 CH₂CH₂ 2-CF₃, 4,5-F₂ 4-C(O)C₆H₅ 1.316 CH₂CH₂2-CF₃, 4,5-F₂ 2-C(NOCH₃)C₆H₅ 1.317 CH₂CH₂ 2-CF₃, 4,5-F₂ 3-C(NOCH₃)C₆H₅1.318 CH₂CH₂ 2-CF₃, 4,5-F₂ 4-C(NOCH₃)C₆H₅ 1.319 CH₂CH₂ 2-CF₃, 4,5-F₂2-CH(CN)C₆H₅ 1.320 CH₂CH₂ 2-CF₃, 4,5-F₂ 3-CH(CN)C₆H₅ 1.321 CH₂CH₂ 2-CF₃,4,5-F₂ 4-CH(CN)C₆H₅ 1.322 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ H 1.323 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 2-F 1.324 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 3-F1.325 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 4-F 1.326 CH₂CH₂ 2-O-cyclopropyl,4,5-F₂ 2-Cl 1.327 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 3-Cl 1.328 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 4-Cl 1.329 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 2-CH₃1.330 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 3-CH₃ 1.331 CH₂CH₂ 2-O-cyclopropyl,4,5-F₂ 4-CH₃ 1.332 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 2-CF₃ 1.333 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 3-CF₃ 1.334 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 4-CF₃1.335 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 2-OCF₃ 1.336 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 3-OCF₃ 1.337 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂4-OCF₃ 1.338 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 2-OCF₂CF₂H 1.339 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 3-OCF₂CF₂H 1.340 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂4-OCF₂CF₂H 1.341 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 2-OCF₂CF₃ 1.342 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 3-OCF₂CF₃ 1.343 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂4-OCF₂CF₃ 1.344 CH₂CH₂ 2-O-cyclopropyl, 4,5-F_(2,) 2-OC₆H₅ 1.345 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 3-OC₆H₅ 1.346 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂4-OC₆H₅ 1.347 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 2-NHC₆H₅ 1.348 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 3-NHC₆H₅ 1.349 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂4-NHC₆H₅ 1.350 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 2-NCH₃C₆H₅ 1.351 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 3-NCH₃C₆H₅ 1.352 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂4-NCH₃C₆H₅ 1.353 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 2-C(O)C₆H₅ 1.354 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 3-C(O)C₆H₅ 1.355 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂4-C(O)C₆H₅ 1.356 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 2-C(NOCH₃)C₆H₅ 1.357CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 3-C(NOCH₃)C₆H₅ 1.358 CH₂CH₂2-O-cyclopropyl, 4,5-F₂ 4-C(NOCH₃)C₆H₅ 1.359 CH₂CH₂ 2-O-cyclopropyl,4,5-F₂ 2-CH(CN)C₆H₅ 1.360 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 3-CH(CN)C₆H₅1.361 CH₂CH₂ 2-O-cyclopropyl, 4,5-F₂ 4-CH(CN)C₆H₅ 1.362 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ H 1.363 CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂2-F 1.364 CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-F 1.365 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-F 1.366 CH₂CH₂ 2-N(CH₃)-cyclopropyl,4,5-F₂ 2-Cl 1.367 CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-Cl 1.368 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-Cl 1.369 CH₂CH₂ 2-N(CH₃)-cyclopropyl,4,5-F₂ 2-CH₃ 1.370 CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-CH₃ 1.371CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-CH₃ 1.372 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-CF₃ 1.373 CH₂CH₂ 2-N(CH₃)-cyclopropyl,4,5-F₂ 3-CF₃ 1.374 CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-CF₃ 1.375CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-OCF₃ 1.376 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-OCF₃ 1.377 CH₂CH₂ 2-N(CH₃)-cyclopropyl,4,5-F₂ 4-OCF₃ 1.378 CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-OCF₂CF₂H 1.379CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-OCF₂CF₂H 1.380 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-OCF₂CF₂H 1.381 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-OCF₂CF₃ 1.382 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-OCF₂CF₃ 1.383 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-OCF₂CF₃ 1.384 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-OC₆H₅ 1.385 CH₂CH₂ 2-N(CH₃)-cyclopropyl,4,5-F₂ 3-OC₆H₅ 1.386 CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-OC₆H₅ 1.387CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-NHC₆H₅ 1.388 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-NHC₆H₅ 1.389 CH₂CH₂ 2-N(CH₃)-cyclopropyl,4,5-F₂ 4-NHC₆H₅ 1.390 CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-NCH₃C₆H₅1.391 CH₂CH₂ 2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-NCH₃C₆H₅ 1.392 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-NCH₃C₆H₅ 1.393 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-C(O)C₆H₅ 1.394 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-C(O)C₆H₅ 1.395 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-C(O)C₆H₅ 1.396 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-C(NOCH₃)C₆H₅ 1.397 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-C(NOCH₃)C₆H₅ 1.398 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-C(NOCH₃)C₆H₅ 1.399 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 2-CH(CN)C₆H₅ 1.400 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 3-CH(CN)C₆H₅ 1.401 CH₂CH₂2-N(CH₃)-cyclopropyl, 4,5-F₂ 4-CH(CN)C₆H₅ 1.402 CH₂CH₂ 2-Br, 4,5-F₂ H1.403 CH₂CH₂ 2-Br, 4,5-F₂ 2-F 1.404 CH₂CH₂ 2-Br, 4,5-F₂ 3-F 1.405 CH₂CH₂2-Br, 4,5-F₂ 4-F 1.406 CH₂CH₂ 2-Br, 4,5-F₂ 2-Cl 1.407 CH₂CH₂ 2-Br,4,5-F₂ 3-Cl 1.408 CH₂CH₂ 2-Br, 4,5-F₂ 4-Cl 1.409 CH₂CH₂ 2-Br, 4,5-F₂2-CH₃ 1.410 CH₂CH₂ 2-Br, 4,5-F₂ 3-CH₃ 1.411 CH₂CH₂ 2-Br, 4,5-F₂ 4-CH₃1.412 CH₂CH₂ 2-Br, 4,5-F₂ 2-CF₃ 1.413 CH₂CH₂ 2-Br, 4,5-F₂ 3-CF₃ 1.414CH₂CH₂ 2-Br, 4,5-F₂ 4-CF₃ 1.415 CH₂CH₂ 2-Br, 4,5-F₂ 2-OCF₃ 1.416 CH₂CH₂2-Br, 4,5-F₂ 3-OCF₃ 1.417 CH₂CH₂ 2-Br, 4,5-F₂ 4-OCF₃ 1.418 CH₂CH₂ 2-Br,4,5-F₂ 2-OCF₂CF₂H 1.419 CH₂CH₂ 2-Br, 4,5-F₂ 3-OCF₂CF₂H 1.420 CH₂CH₂2-Br, 4,5-F₂ 4-OCF₂CF₂H 1.421 CH₂CH₂ 2-Br, 4,5-F₂ 2-OCF₂CF₃ 1.422 CH₂CH₂2-Br, 4,5-F₂ 3-OCF₂CF₃ 1.423 CH₂CH₂ 2-Br, 4,5-F₂ 4-OCF₂CF₃ 1.424 CH₂CH₂2-Br, 4,5-F₂ 2-OC₆H₅ 1.425 CH₂CH₂ 2-Br, 4,5-F₂ 3-OC₆H₅ 1.426 CH₂CH₂2-Br, 4,5-F₂ 4-OC₆H₅ 1.427 CH₂CH₂ 2-Br, 4,5-F₂ 2-NHC₆H₅ 1.428 CH₂CH₂2-Br, 4,5-F₂ 3-NHC₆H₅ 1.429 CH₂CH₂ 2-Br, 4,5-F₂ 4-NHC₆H₅ 1.430 CH₂CH₂2-Br, 4,5-F₂ 2-NCH₃C₆H₅ 1.431 CH₂CH₂ 2-Br, 4,5-F₂ 3-NCH₃C₆H₅ 1.432CH₂CH₂ 2-Br, 4,5-F₂ 4-NCH₃C₆H₅ 1.433 CH₂CH₂ 2-Br, 4,5-F₂ 2-C(O)C₆H₅1.434 CH₂CH₂ 2-Br, 4,5-F₂ 3-C(O)C₆H₅ 1.435 CH₂CH₂ 2-Br, 4,5-F₂4-C(O)C₆H₅ 1.436 CH₂CH₂ 2-Br, 4,5-F₂ 2-C(NOCH₃)C₆H₅ 1.437 CH₂CH₂ 2-Br,4,5-F₂ 3-C(NOCH₃)C₆H₅ 1.438 CH₂CH₂ 2-Br, 4,5-F₂ 4-C(NOCH₃)C₆H₅ 1.439CH₂CH₂ 2-Br, 4,5-F₂ 2-CH(CN)C₆H₅ 1.440 CH₂CH₂ 2-Br, 4,5-F₂ 3-CH(CN)C₆H₅1.441 CH₂CH₂ 2-Br, 4,5-F₂ 4-CH(CN)C₆H₅

BIOLOGICAL EXAMPLES

1. In Vivo Test Against Trichostrongylus Colubriformis and HaemnonchusContortus in Mongolian Gerbils (Meriones unguiculatus) by PeroralAdministration

Six- to eight-week-old Mongolian gerbils are infected, usingmanufactured feed, with in each case approximately 2000 larvae of the3rd stage of T. colubriformis and H. contortus. Six days afterinfecting, the gerbils are lightly anaesthetized with N₂O and aretreated by peroral administration with the test compounds, dissolved ina mixture of 2 parts of DMSO and 1 part of polyethylene glycol (PEG300), with amounts of 100, 32 and 10-0.1 mg/kg. On day 9 (3 days aftertreating), when most of the H. contortus larvae still existing are inthe late 4th stage and most of the T. colubriformis are immature adults,the gerbils are sacrificed in order to count the worms. The activity iscalculated in % reduction in the number of worms in each gerbil bycomparison with the geometric mean of the number of worms from 8infected and untreated gerbils.

In this test, a large decrease in the nematode infestation is obtainedwith compounds of the formula I, in particular from Table 1.

The following test methods can be employed in investigating theinsecticidal and/or acaricidal action of the compounds of the formula Ion animals and plants.

2. Action Against L₁ Larvae of Lucilia sericata

1 ml of an aqueous suspension of the active substance to be tested isthus mixed at approximately 50° C. with 3 ml of a special medium forraising larvae, so that a homogenate with an active ingredient contentof either 250 or 125 ppm is formed. Approximately 30 Lucilia larvae (L₁)are introduced into each test tube sample. After 4 days, the mortalityrate is determined.

3. Acaricidal Action Against Boophilus microplus (Biarra strain)

An adhesive tape is attached horizontally to a PVC plate such that 10female Boophilus microplus ticks (Biarra strain) which have suckedthemselves full of blood can be adhesively attached to the tape viatheir backs in a row, next to one another. Each tick is injected, usingan injection needle, with 1 μl of a liquid which is a 1:1 mixture ofpolyethylene glycol and acetone and in which a certain amount of activeingredient of alternatively 1, 0.1 or 0.01 μg per tick is dissolved.Control animals receive an injection not comprising an activeingredient. After the treatment, the animals are kept in an insectariumunder standard conditions at approximately 28° C. and 80% relativehumidity until egg laying has occurred and the larvae have hatched fromthe eggs of the control animals. The activity of a test substance isdetermined using the IR₉₀, i.e. that dose of active ingredient isascertained at which, after 30 days, 9 out of 10 female ticks (=90%) layeggs which are not able to hatch.

4. In Vitro Activity Against Fed Boophilus microplus Females (Biarra):

4×10 fed female ticks of the OP-resistant Biarra strain are attached toan adhesive tape and are covered for 1 h with a wad of cotton which hasbeen impregnated with an emulsion or suspension of the test compound inconcentrations in each case of 500, 125, 31 and 8 ppm. The mortality,egg laying and larval hatching are evaluated 28 days later.

An indication of the activity of the test compounds is the number of thefemales which

-   -   quickly die, before laying eggs,    -   survive for some time, without laying eggs,    -   lay eggs in which no embryos develop,    -   lay eggs in which embryos develop but from which no larvae        hatch, and    -   lay eggs in which embryos develop and from which larvae hatch        normally in 26 to 27 days.        5. In Vitro Activity Against Nymphs of Amblyomma hebraeum

About 5 hungry nymphs are placed in a polystyrene test tube comprising 2ml of the test compound in solution, suspension or emulsion.

After immersing for 10 minutes and shaking for 2×10 seconds on a vortexmixer, the test tubes are plugged with a thick wad of cotton wool andare inverted. As soon as all the liquid has been soaked up by the wad ofcotton, the wad is pushed halfway into the still inverted test tube, sothat most of the liquid is squeezed out of the wad of cotton and flowsinto a petri dish placed underneath.

The test tubes are now, until evaluation, stored at ambient temperaturein a room lit by daylight. After 14 days, the test tubes are immersed ina beaker of boiling water. If, in reaction to the heat, the ticks beginto move, the test substance is inactive at the test concentration;otherwise, the ticks are considered to be dead and the test substance isconsidered to be active at the test concentration. All substances aretested in a concentration range from 0.1 to 100 ppm.

6. Action Against Dermanyssus gallinae

2 to 3 ml of a solution comprising 10 ppm of active ingredient andapproximately 200 mites (Dermanyssus gallinae) at various developmentstages are placed in a glass vessel open at the top. The vessel issubsequently plugged with a wad of cotton, shaken for 10 minutes, untilthe mites have been completely wetted, and then briefly inverted, sothat the remaining test solution can be absorbed by the cotton wool.After 3 days, the mortality of the mites is ascertained by counting thedead individuals and is given in percent.

7. Action Against Musca domestica

A sugar cube is treated with a solution of the test substance such thatthe concentration of test substance in the sugar, after dryingovernight, is 250 ppm. This treated cube is placed with a wet wad ofcotton and 10 adult Musca domestica of an OP-resistant strain on analuminium dish, is covered with a beaker and is incubated at 25° C. Themortality rate is determined after 24 hours.

1-33. (canceled)
 34. A method for the preparation of a compound offormula II

which is known or can be prepared by analogy to relevant known compoundsand in which Ar₂ is unsubstituted or mono- or polysubstituted phenyl, inwhich the substituents can be independent of one another and are chosenfrom the group consisting of halogen, nitro, cyano, C₁-C₆alkyl,halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy, C₂-C₆alkenyl,halO-C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₃-C₆cycloalkyloxy,C₃-C₆cycloalkylamino, C₃-C₆cycloalkylthio, C₂-C₆alkenyloxy,halo-C₂-C₆alkenyloxy, C₁-C₆alkylthio, halo-C₁-C₆alkylthio,C₁-C₆alkylsulfonyloxy, halo-C₁-C₆alkylsulfonyloxy, C₁-C₆alkylsulfinyl,halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, halo-C₁-C₆alkylsulfonyl,C₂-C₆alkenylthio, halo-C₂-C₆alkenylthio, C₂-C₆alkenylsulfinyl,halo-C₂-C₆alkenylsulfinyl, C₂-C₆alkenylsulfonyl,halo-C₂-C₆alkenylsulfonyl, C₁-C₆alkylamino, di-C₁-C₆alkylamino,C₁-C₆alkylsulfonylamino, halo-C₁-C₆alkylsufonylamino,C₁-C₆alkylcarbonyl, halo-C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆alkylaminocarbonyl and di-C₁-C₆alkylaminocarbonyl; unsubstituted ormono- or polysubstituted phenylamino; unsubstituted or mono- orpolysubstituted phenylcarbonyl; unsubstituted or mono- orpolysubstituted phenylmethoxymino; unsubstituted or mono- orpolysubstituted phenylhydroxymethyl; unsubstituted or mono- orpolysubstituted 1-phenyl-1-hydroxyethyl; unsubstituted or mono- orpolysubstituted phenylchloromethyl; unsubstituted or mono- orpolysubstituted phenylcyanomethyl; unsubstituted or mono- orpolysubstituted phenyl, in which the substituents in each case can beindependent of one another and are chosen from the group consisting ofhalogen, nitro, cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,halo-C₁-C₆alkoxy, C₁-C₆alkylthio, halo-C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, halo-C₁-C₆alkylsufinyl, C₁-C₆alkylsulfonyl andhalo-C₁-C₆alkylsulfonyl; unsubstituted or mono- or polysubstitutedphenoxy, in which the substituents can be independent of one another andare chosen from the group consisting of halogen, nitro, cyano,C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl and halo-C₁-C₆alkylsulfonyl;unsubstituted or mono- or polysubstituted phenylacetylenyl, in which thesubstituents can be independent of one another and are chosen from thegroup consisting of halogen, nitro, cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl,C₁-C₆alkoxy, halo-C₁-C₆alkoxy, C₁-C₆alkylthio, halo-C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, halo-C₁-C₆alkylsufinyl, C₁-C₆alkylsulfonyl andhalo-C₁-C₆alkylsulfonyl; and unsubstituted or mono- or polysubstitutedpyridyloxy, in which the substituents can be independent of one anotherand are chosen from the group consisting of substituents can beindependent of one another and are chosen from the group consisting ofhalogen, nitro, cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,halo-C₁-C₆alkoxy, C₁-C₆alkylthio, halo-C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl andhalo-C₁-C₆alkylsulfonyl; unsubstituted or mono- or polysubstitutedhetaryl, in which the substituents can be independent of one another andare chosen from the group consisting of halogen, nitro, cyano,C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₂-C₆alkenyloxy, halo-C₂-C₆alkenyloxy, C₁-C₆alkylthio,halo-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, halo-C₁-C₆alkylsulfinyl,C₂-C₆alkenylthio, halo-C₂-C₆alkenylthio, C₂-C₆alkenylsulfinyl,halo-C₂-C₆alkenylsulfinyl, C₁-C₆alkylsulfonyl, halo-C₁-C₆alkylsulfonyl,C₂-C₆alkenylsulfonyl, halo-C₂-C₆alkenylsulfonyl, C₁-C₆alkylamino anddi-C₁-C₆alkylamino; or unsubstituted or mono- or polysubstitutednaphthyl or quinolyl, in which the substituents can be independent ofone another and are chosen from the group consisting of halogen, nitro,cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₂-C₆alkenyloxy, halo-C₂-C₆alkenyloxy, C₁-C₆alkylthio,halo-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, halo-C₁-C₆alkylsulfinyl,C₂-C₆alkenylthio, halo-C₂-C₆alkenylthio, C₂-C₆alkenylsulfinyl,halo-C₂-C₆alkenylsulfinyl, C₁-C₆alkylsulfonyl, halo-C₁-C₆alkylsulfonyl,C₂-C₆alkenylsulfonyl, halo-C₂-C₆alkenylsulfonyl, C₁-C₆alkylamino anddi-C₁-C₆alkylamino; R₁ is hydrogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, allylor C₁-C₆alkoxymethyl; R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are either,independently of one another, hydrogen, halogen, unsubstituted or mono-or polyhalogenated C₁-C₆alkyl, unsubstituted or mono- or polyhalogenatedC₂-C₆alkenyl, unsubstituted or mono- or polyhalogenated C₂-C₆alkynyl;unsubstituted or mono- or polysubstituted C₁-C₆alkoxy, unsubstituted ormono- or polysubstituted halo-C₁-C₆alkoxy, unsubstituted or mono- orpolysubstituted C₃-C₆cycloalkyl, in which the substituents in each casecan be independent of one another and are chosen from the groupconsisting of halogen and C₁-C₆alkyl; or unsubstituted or mono- orpolysubstituted phenyl, in which the substituents can be independent ofone another and are chosen from the group consisting of halogen, nitro,cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,halo-C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, halo-C₁-C₆alkylsulfonyl,C₁-C₆alkylamino or di-C₁-C₆alkylamino; or R₂ and R₃ are jointlyC₂-C₆alkylene; and X is C(R₃)(R₄)—C(R₅)(R₆) or C(R₇)═C(R₈), in each casein the free form or in the salt form, which comprises the reaction of acompound of the formula IV

which is known or can be prepared by analogy to relevant known compoundsand in which R₂, X and Ar₂ are as defined above, with an inorganic ororganic cyanide and a compound of the formula R₁—NH₂, which is known orcan be prepared by analogy to relevant known compounds and in which R₁is as defined as above, and in each case, if desired, the conversion ofa compound of the formula II obtainable according to the process or inanother way, in each case in the free form or in the salt form, toanother compound of the formula II, the separation of a mixture ofisomers obtainable according to the process and the isolation of thedesired isomer and/or the conversion of a free compound of the formulaII obtainable according to the process to a salt or the conversion of asalt of a compound of the formula II obtainable according to the processto the free compound of the formula II or to another salt.